Azoline compounds substituted by a condensed ring system

ABSTRACT

The present invention relates to compounds of formula I wherein the variables are as defined in the claims and the description. The invention further relates to the use of these compounds for controlling invertebrate pests and to plant propagation material and [o an agricultural and a veterinary composition comprising said compounds. The invention also relates to novel compounds useful as intermediate compounds in the preparation of compounds I.

This application is a continuation of U.S. application Ser. No.15/538,499, filed Jun. 21, 2017 (now U.S. Pat. No. 10,093,662). U.S.application Ser. No. 15/538,499 is a National Stage Application ofInternational Application No. PCT/EP2015/080819, filed Dec. 21, 2015.U.S. application Ser. No. 15/538,499 also claims the priority benefit ofU.S. Provisional Application No. 62/095,071, filed Dec. 22, 2014, theentirety of all of which are hereby incorporated herein by reference.

The present invention relates to azoline compounds substituted by acondensed ring system which are useful for combating or controllinginvertebrate pests, in particular arthropod pests and nematodes. Theinvention also relates to a method for controlling invertebrate pests byusing these compounds and to plant propagation material and to anagricultural and a veterinary composition comprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an on-going need for new agents for combating invertebrate pests, inparticular insects, arachnids and nematodes.

Related compounds are described in WO 2013/026929, WO 2012/163959, WO2012/007426, WO 2011/067272, WO 2010/149506, WO 2010/020522, WO2009/080250, EP-A-1731512, JP-A-2007091708 and JP-A-2008133273. However,these documents do not describe compounds having the characteristicsubstituents and substituents' arrangement as claimed in the presentinvention.

It is an object of the present invention to provide compounds that havea good pesticidal activity, in particular insecticidal activity, andshow a broad activity spectrum against a large number of differentinvertebrate pests, especially against difficult to control arthropodpests and/or nematodes.

The object of the present invention is moreover to provide compoundswhich are less persistent, bioaccumulative and/or toxic than thecompounds of the prior art. Especially isoxazoline insecticides of theprior art show a high persistency in the soil and thus accumulate there.

It has been found that these objectives can be achieved by azolinecompounds of the formula I below, by their stereoisomers, their N-oxidesand by their salts, in particular their agriculturally or veterinarilyacceptable salts.

Therefore, in a first aspect, the invention relates to azoline compoundsof the formula I

wherein

-   X¹ is O or CH₂;-   A is a group A¹ or A²;    -   wherein    -   A¹ is a group of following formula:

-   -   -   wherein        -   # denotes the bond to the aromatic ring of formula (I); and        -   W is selected from O and S; and

    -   A² is a group —C(R^(7a))(R^(7b))—N(R⁵²)—C(═O)—R⁶²

-   B¹, B², B³, B⁴ and B⁵ are independently selected from the group    consisting of N and CR², with the proviso that at most one of B¹,    B², B³, B⁴ and B⁵ is N;

-   R^(g1) and R^(g2) form together a bridging group selected from    —CH₂CH₂O—, —OCH₂CH₂—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S(O)_(p)—,    —S(O)_(p)CH₂CH₂—, —CH₂S(O)_(p)CH₂—, —S(O)_(p)CH₂S(O)_(p)—,    —OCH₂S(O)_(p)—, —S(O)_(p)CH₂O—, —OCH₂CH₂CH₂—, —CH₂CH₂CH₂O—,    —CH₂OCH₂CH₂—, —CH₂CH₂OCH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—, —CH₂OCH₂O—,    —S(O)_(p)CH₂CH₂CH₂—, —CH₂CH₂CH₂S(O)_(p)—, —CH₂S(O)_(p)CH₂CH₂—,    —CH₂CH₂S(O)_(p)CH₂—, —S(O)_(p)CH₂CH₂S(O)_(p)—,    —S(O)_(p)CH₂S(O)_(p)CH₂—, —CH₂S(O)_(p)CH₂S(O)_(p)—,    —S(O)_(p)CH₂CH₂O—, —OCH₂CH₂S(O)_(p)—, —S(O)_(p)CH₂OCH₂—,    —OCH₂S(O)_(p)CH₂—, —CH₂OCH₂S(O)_(p)— and —CH₂S(O)_(p)CH₂O—;    -   where p is 0, 1 or 2    -   where the hydrogen atoms of the above groups may be replaced by        one or more substituents selected from halogen, methyl,        halogenated methyl, hydroxyl, methoxy and halogenated methoxy;        and/or one or two CH₂ groups of the above groups may be replaced        by a C═O group;

-   R¹ is C₁-haloalkyl;

-   each R² is independently selected from the group consisting of    hydrogen, halogen, C₁-C₂-haloalkoxy and C₁-C₂-haloalkyl;

-   R^(3a) and R^(3b), independently of each other, are selected from    hydrogen and halogen;

-   R^(7a) and R^(7b), independently of each other, are selected from    hydrogen, cyano, methyl and C₁-haloalkyl;

-   R⁵¹ and R⁵², independently of each other, are selected from the    group consisting of hydrogen, C₁-C₃-alkyl, C₂-C₃-alkenyl,    C₂-C₃-alkynyl, C₁-C₆-alkoxymethyl and CH₂—CN;

-   R⁶¹ is selected from the group consisting of hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkyl which carries one or two radicals R⁸¹,    C₁-C₆-haloalkyl which carries one radical R⁸¹, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 or 2 CN substituents; C₃-C₆-halocycloalkyl;    —N(R^(110a))R^(101b), —CH═NOR⁹¹, phenyl which may be substituted    with 1, 2, 3, 4, or 5 substituents R¹⁶, and a heterocyclic ring    selected from rings E-1 to E-63

-   -   where in rings E-1 to E-63    -   the zigzag line denotes the attachment point to the remainder of        the molecule;    -   k is 0, 1, 2 or 3;    -   n is 0, 1 or 2; and    -   R¹⁶ is as defined below;

-   R⁶² is selected from the group consisting of hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkyl substituted by one or two radicals R⁸²,    C₁-C₆-haloalkyl which carries one radical R⁸², C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₆-cycloalkyl which optionally carries a CN substituent,    C₃-C₆-halocycloalkyl, —N(R^(102a))R^(102b),    -   —C(═O)N(R^(112a))R^(112b), —CH═NOR⁹², phenyl which is optionally        substituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a        heterocyclic ring selected from rings of formulae E-1 to E-63 as        defined above;

-   each R⁸¹ is independently selected from OH, CN, C₃-C₈-cycloalkyl    which optionally carries a CN or C₁-haloalkyl substituent,    C₃-C₆-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(101c))R^(101d), phenyl,    optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a    heterocyclic ring selected from rings E-1 to E-63 as defined above;

-   each R⁸² is independently selected from OH, CN, C₃-C₆-cycloalkyl    which optionally carries a CN or C₁-haloalkyl substituent,    C₃-C₆-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102c))R^(102d), phenyl,    optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a    heterocyclic ring selected from rings E-1 to E-63 as defined above;

-   R⁹¹ and R⁹², independently of each other, are selected from    hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;

-   R^(101a), R^(102a), R^(102c) and R^(112a), independently of each    other, are selected from hydrogen and C₁-C₆-alkyl;

-   R^(101b) is selected from hydrogen,    -   —C(═O)N(R^(14a))R^(14b), phenyl, optionally substituted with 1,        2, 3, 4 or 5 substituents R¹⁶; and a heterocyclic ring selected        from rings of formulae E-1 to E-42 as defined above;

-   R^(102b) is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    CH₂—CN, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl,    C₃-C₆-halocycloalkylmethyl, phenyl, optionally substituted with 1,    2, 3, 4 or 5 substituents R¹⁶; and a heterocyclic ring selected from    rings of formulae E-1 to E-42 as defined above;

-   R^(101c) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;

-   R^(101d) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl,    C₃-C₆-halocycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl    which is optionally substituted with 1, 2, 3, 4 or 5 substituents    selected from the group consisting of halogen, cyano, nitro,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio and C₁-C₄-haloalkylthio; and a heterocyclic ring    selected from rings of formulae E-1 to E-63 as defined above;

-   R^(102d) and R^(112b), independently of each other, are selected    from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₆-cycloalkyl which optionally carries a CN substituent,    C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl and    C₃-C₆-halocycloalkylmethyl;

-   R^(14a) is selected from the group consisting of hydrogen and    C₁-C₆-alkyl;

-   R^(14b) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl,    C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and

-   each R¹⁶ is independently selected from the group consisting of    halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-halocycloalkyl-C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl,    C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and    di-(C₁-C₄-alkyl)aminocarbonyl; or    -   two R¹⁶ present on the same carbon atom of a saturated ring may        form together ═O or ═S; or    -   two R¹⁶ present on the same S or SO ring member of a        heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;        and the N-oxides, stereoisomers and agriculturally or        veterinarily acceptable salts thereof.

The present invention also provides an agricultural compositioncomprising at least one compound of the formula I as defined herein, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof and at least one inert liquid and/or solid agriculturallyacceptable carrier.

The present invention also provides a veterinary composition comprisingat least one compound of the formula I as defined herein, a stereoisomerthereof and/or at least one veterinarily acceptable salt thereof and atleast one inert liquid and/or solid veterinarily acceptable carrier.

The present invention also provides a method for controllinginvertebrate pests which method comprises treating the pests, their foodsupply, their habitat or their breeding ground or a cultivated plant,plant propagation materials (such as seed), soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, cultivated plants, plant propagation materials (such asseed), soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula I, a stereoisomer thereof and/or at least one agriculturallyacceptable salt thereof as defined herein. In a specific embodiment, themethod is not for treating the human or animal body; i.e. the foodsupply, habitat, breeding ground, area, material, environment, soils,surfaces or spaces is not a human or animal body.

The method serves in particular for protecting plants from attack orinfestation by invertebrate pests, and thus comprises treating theplants with a pesticidally effective amount of at least one compound ofthe formula I as defined above, a stereoisomer thereof and/or at leastone agriculturally acceptable salt thereof. The method further serves inparticular for protecting plant propagation material and/or the plantswhich grow therefrom from attack or infestation by invertebrate pests,and thus comprises treating the plant propagation material with apesticidally effective amount of at least one compound of the formula Ias defined above, a stereoisomer thereof and/or at least oneagriculturally acceptable salt thereof.

The present invention also relates to plant propagation material, inparticular seed, comprising at least one compound of formula I, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof as defined herein.

The present invention further relates to a method for treating orprotecting an animal from infestation or infection by parasites(invertebrate pests) which comprises bringing the animal in contact witha parasiticidally/pesticidally effective amount of a compound of theformula I, a stereoisomer thereof and/or at least one veterinarilyacceptable salt thereof as defined herein. Bringing the animal incontact with the compound I, its salt or the veterinary composition ofthe invention means applying or administering it to the animal.

The present invention further relates to compounds of the formula I,stereoisomers thereof and/or veterinarily acceptable salts thereof asdefined herein for use as a medicament, especially for use as amedicament for treating or protecting an animal from infestation orinfection by parasites (invertebrate pests).

The term “steroisomers” encompasses both optical isomers, such asenantiomers or diastereomers, the latter existing due to more than onecenter of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom of the isoxazoline or pyrroline ringcarrying radical R¹. The invention provides both the pure enantiomers ordiastereomers and their mixtures and the use according to the inventionof the pure enantiomers or diastereomers of the compound I or itsmixtures. Suitable compounds of the formula I also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

In a specific embodiment, the compounds I are present in form of amixture of compounds I.1 and I.2

where compound I.1 is present in an amount of more than 50% by weight,in particular of at least 70% by weight, specifically of at least 90% byweight, based on the total weight of compounds I.1 and I.2.

The term N-oxides relates to a form of compounds I in which at least onenitrogen atom is present in oxidized form (as NO). To be more precise,it relates to any compound of the present invention which has at leastone tertiary nitrogen atom that is oxidized to an N-oxide moiety.N-oxides of compounds I can in particular be prepared by oxidizing e.g.the ring nitrogen atom of the isoxazoline/pyrroline moiety and/or of anynitrogen-containing heterocyclic group present in group A with asuitable oxidizing agent, such as peroxo carboxylic acids or otherperoxides. The person skilled in the art knows if and in which positionscompounds of the present invention may form N-oxides.

The compounds of the present invention may be amorphous or may exist inone ore more different crystalline states (polymorphs) which may have adifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of the formula I, mixtures ofdifferent crystalline states of the respective compound I, as well asamorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, do not have any adverse effect on the actionof the compounds according to the present invention. Suitable cationsare in particular the ions of the alkali metals, preferably lithium,sodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH⁴⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzyl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formulae I withan acid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of thosecations or anions which are known and accepted in the art for theformation of salts for veterinary use. Suitable acid addition salts,e.g. formed by compounds of formula I containing a basic nitrogen atom,e.g. an amino group, include salts with inorganic acids, for examplehydrochlorids, sulphates, phosphates, and nitrates and salts of organicacids for example acetic acid, maleic acid, dimaleic acid, fumaric acid,difumaric acid, methane sulfenic acid, methane sulfonic acid, andsuccinic acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. The plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting. Said youngplants may also be protected before transplantation by a total orpartial treatment by immersion or pouring.

The term “plants” comprises any types of plants including“non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species orrelated species or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf.http://www.bio.org/speeches/pubs/er/agri_products.asp). Geneticallymodified plants are plants, which genetic material has been so modifiedby the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted post-translational modificationof protein(s), oligo- or polypeptides e. g. by glycosylation or polymeradditions such as prenylated, acetylated or farnesylated moieties or PEGmoieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e. g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxyl-phenylpyruvatedioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors;acetolactate synthase (ALS) inhibitors such as sulfonyl ureas orimidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS)inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitorssuch as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipidbiosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as aresult of conventional methods of breeding or genetic engineering.Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or ACCase inhibitors. These herbicide resistancetechnologies are e. g. described in Pest Managem. Sci. 61, 2005, 246;61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008,326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.58, 2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e. g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e. g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e. g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofathropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus(corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from themexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl and the likerefers to saturated straight-chain or branched hydrocarbon radicalshaving 1 to 2 (“C₁-C₂-alkyl”), 1 to 3 (“C₁-C₃-alkyl”), 1 to 4(“C₁-C₄-alkyl”), 2 to 4 (“C₂-C₄-alkyl”), 1 to 6 (“C₁-C₆-alkyl”), 1 to 8(“C₁-C₈-alkyl”) or 1 to 10 (“C₁-C₁₀-alkyl”) carbon atoms. C₁-C₂-Alkyl ismethyl or ethyl. C₁-C₃-Alkyl is additionally propyl and isopropyl.C₁-C₄-Alkyl is additionally butyl, 1-methylpropyl (sec-butyl),2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl). C₁-C₆-Alkylis additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or1-ethyl-2-methylpropyl. C₁-C₈-Alkyl is additionally also, for example,heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C₁-C₁₀-Alkylis additionally also, for example, nonyl, decyl and positional isomersthereof. C₂-C₄-Alkyl is ethyl, propyl, isopropyl, n-butyl,1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or1,1-dimethylethyl (tert-butyl).

The term “haloalkyl” as used herein, which is also expressed as “alkylwhich is partially or fully halogenated”, refers to straight-chain orbranched alkyl groups having 1 (“C₁-haloalkyl”; also termed “halogenatedmethyl” or “halomethyl”), 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3(“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”), 1 to 6(“C₁-C₆-haloalkyl”), 1 to 8 (“C₁-C₈-haloalkyl”) or 1 to 10(“C₁-C₁₀-haloalkyl”) carbon atoms (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above: C₁-C₂-haloalkyl, such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl,2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl,1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl,heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and thelike. Examples for C₁-C₄-haloalkyl are, apart those mentioned forC₁-C₃-haloalkyl, 4-chlorobutyl and the like.

“Halomethyl” or “halogenated methyl” or “C₁-haloalkyl” is methyl inwhich 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms.Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl,trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl and the like.

C₂-C₄-Alkyl substituted with 1 or 2 fluorine atoms is C₂-C₄-alkyl, where1 or 2 of the hydrogen atoms are replaced by fluorine atoms. Examplesare 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1,2-difluoroethyl,2,2-difluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl,1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl,1,2-difluoropropyl, 1,3-difluoropropyl, 2,3-difluoropropyl,1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, and thelike.

The term “alkenyl” as used herein refers to monounsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”), 2 to 6 (“C₂-C₆-alkenyl”), 2to 8 (“C₂-C₈-alkenyl”) or 2 to 10 (“C₂-C₁₀-alkenyl”) carbon atoms and adouble bond in any position, for example C₂-C₃-alkenyl, such as ethenyl,1-propenyl, 2-propenyl or 1-methylethenyl; C₂-C₄-alkenyl, such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenylor 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₁₀-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positionalisomers thereof.

The term “haloalkenyl” as used herein, which is also expressed as“alkenyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkenyl”), 2 to 4 (“C₂-C₄-haloalkenyl”), 2 to 6(“C₂-C₆-haloalkenyl”), 2 to 8 (“C₂-C₆-haloalkenyl”) or 2 to 10(“C₂-C₁₀-haloalkenyl”) carbon atoms and a double bond in any position(as mentioned above), where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine, for example chlorovinyl, chloroallyl andthe like.

The term “alkynyl” as used herein refers to straight-chain or branchedhydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4(“C₂-C₄-alkynyl”), 2 to 6 (“C₂-C₆-alkynyl”), 2 to 8 (“C₂-C₈-alkynyl”),or 2 to 10 (“C₂-C₁₀-alkynyl”) carbon atoms and one or two triple bondsin any position, for example C₂-C₃-alkynyl, such as ethynyl, 1-propynylor 2-propynyl; C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like,C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and the like;

The term “haloalkynyl” as used herein, which is also expressed as“alkynyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkynyl”), 2 to 4 (“C₂-C₄-haloalkynyl”), 3 to 4(“C₃-C₄-haloalkynyl”), 2 to 6 (“C₂-C₆-haloalkynyl”), 2 to 8(“C₂-C₈-haloalkynyl”) or 2 to 10 (“C₂-C₁₀-haloalkynyl”) carbon atoms andone or two triple bonds in any position (as mentioned above), where someor all of the hydrogen atoms in these groups are replaced by halogenatoms as mentioned above, in particular fluorine, chlorine and bromine;

The term “cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl”), in particular 3 to 6 (“C₃-C₆-cycloalkyl”) or 3 to5 (“C₃-C₅-cycloalkyl”) or 3 to 4 (“C₃-C₄-cycloalkyl”) carbon atoms.Examples of monocyclic radicals having 3 to 4 carbon atoms comprisecyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.Examples of monocyclic radicals having 3 to 6 carbon atoms comprisecyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples ofmonocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.Examples of bicyclic radicals having 7 or 8 carbon atoms comprisebicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl andbicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes amonocyclic saturated hydrocarbon radical.

The term “halocycloalkyl” as used herein, which is also expressed as“cycloalkyl which is partially or fully halogenated”, refers to mono- orbi- or polycyclic saturated hydrocarbon groups having 3 to 8(“C₃-C₈-halocycloalkyl”) or preferably 3 to 6 (“C₃-C₆-halocycloalkyl”)or 3 to 5 (“C₃-C₅-halocycloalkyl”) or 3 to 4 (“C₃-C₄-halocycloalkyl”)carbon ring members (as mentioned above) in which some or all of thehydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl group(“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl group(“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkylgroup (“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably amonocyclic cycloalkyl group) which is bound to the remainder of themolecule via a C₁-C₄-alkyl group, as defined above. Examples forC₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl,cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl andcyclobutylpropyl, Examples for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, apart thosementioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyland cyclohexylpropyl. Examples for C₃-C₈-cycloalkyl-C₁-C₄-alkyl, apartthose mentioned for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, are cycloheptylmethyl,cycloheptylethyl, cyclooctylmethyl and the like.

The term “C₃-C₆-cycloalkyl-methyl” refers to a C₃-C₆-cycloalkyl group asdefined above which is bound to the remainder of the molecule via amethylene group (CH₂). Examples are cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl and cyclohexylmethyl.

The term “C₃-C₈-halocycloalkyl-C₁-C₄-alkyl” refers to aC₃-C₈-halocycloalkyl group as defined above which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.

The term “C₃-C₆-halocycloalkyl-methyl” refers to a C₃-C₆-halocycloalkylgroup as defined above which is bound to the remainder of the moleculevia a methylene group (CH₂).

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is aC₁-C₁₀-alkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Alkoxy is methoxy or ethoxy. C₁-C₃-Alkoxy is additionally, forexample, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy isadditionally, for example, butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is aC₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₄-haloalkoxy” is a C₁-C₄-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is aC₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₁₀-haloalkoxy” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via an oxygen atom. C₁-C₂-Haloalkoxy is, for example,OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy or OC₂F₅. C₁-C₃-Haloalkoxy is additionally, forexample, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy or1-(CH₂Br)-2-bromoethoxy. C₁-C₄-Haloalkoxy is additionally, for example,4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.C₁-C₆-Haloalkoxy is additionally, for example, 5-fluoropentoxy,5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy,6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy ordodecafluorohexoxy.

The term “halogenated methoxy” relates to a C₁-haloalkyl group, asdefined above, attached via an oxygen atom. Examples are OCH₂F, OCHF₂,OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxyor chlorodifluoromethoxy.

The term “C₁-C₃-alkoxy-C₁-C₃-alkyl” as used herein, refers to astraight-chain or branched alkyl group having 1 to 3 carbon atoms, asdefined above, where one hydrogen atom is replaced by a C₁-C₃-alkoxygroup, as defined above. The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as usedherein, refers to a straight-chain or branched alkyl group having 1 to 4carbon atoms, as defined above, where one hydrogen atom is replaced by aC₁-C₄-alkoxy group, as defined above. The term“C₁-C₆-alkoxy-C₁-C₆-alkyl” as used herein, refers to a straight-chain orbranched alkyl group having 1 to 6 carbon atoms, as defined above, whereone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl,1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl,1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl,2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl,2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl,1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl,1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl,2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl,2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl,3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl,3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl,3-tert-butoxypropyl and the like.

The term “C₁-C₄-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₄-alkoxy group, as defined above.The term “C₁-C₆-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

C₁-C₆-Haloalkoxy-C₁-C₆-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 6, especially 1 to 4 carbon atoms(═C₁-C₆-haloalkoxy-C₁-C₄-alkyl), wherein one of the hydrogen atoms isreplaced by a C₁-C₆-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms.C₁-C₄-Haloalkoxy-C₁-C₄-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 4 carbon atoms, wherein one of the hydrogen atoms isreplaced by a C₁-C₄-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms. Examplesare difluoromethoxymethyl (CHF₂OCH₂), trifluoromethoxymethyl,1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl,2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH₃OCF₂),1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term “C₁-C₂-alkylthio” is a C₁-C₂-alkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₃-alkylthio” is a C₁-C₃-alkylgroup, as defined above, attached via a sulfur atom. The term“C₁-C₄-alkylthio” is a C₁-C₄-alkyl group, as defined above, attached viaa sulfur atom. The term “C₁-C₆-alkylthio” is a C₁-C₆-alkyl group, asdefined above, attached via a sulfur atom. The term “C₁-C₁₀-alkylthio”is a C₁-C₁₀-alkyl group, as defined above, attached via a sulfur atom.C₁-C₂-Alkylthio is methylthio or ethylthio. C₁-C₃-Alkylthio isadditionally, for example, n-propylthio or 1-methylethylthio(isopropylthio). C₁-C₄-Alkylthio is additionally, for example,butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio(isobutylthio) or 1,1-dimethylethylthio (tert-butylthio).C₁-C₆-Alkylthio is additionally, for example, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof. C₁-C₁₀-Alkylthio isadditionally, for example, nonylthio, decylthio and positional isomersthereof.

The term “C₁-C₂-haloalkylthio” is a C₁-C₂-haloalkyl group, as definedabove, attached via a sulfur atom. The term “C₁-C₃-haloalkylthio” is aC₁-C₃-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₄-haloalkylthio” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₆-haloalkylthio” is aC₁-C₆-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₁₀-haloalkylthio” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfur atom. C₁-C₂-Haloalkylthio is, for example,SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂, SCCl₃, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio,2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅.C₁-C₃-Haloalkylthio is additionally, for example, 2-fluoropropylthio,3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio,2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅,1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio or1-(CH₂Br)-2-bromoethylthio. C₁-C₄-Haloalkylthio is additionally, forexample, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio.

The term “C₁-C₂-alkylsulfinyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” isa C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. The term “C₁-C₆-alkylsulfinyl” is a C₁-C₆-alkyl group, as definedabove, attached via a sulfinyl [S(O)] group. The term“C₁-C₁₀-alkylsulfinyl” is a C₁-C₁₀-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. C₁-C₂-Alkylsulfinyl ismethylsulfinyl or ethylsulfinyl. C₁-C₄-Alkylsulfinyl is additionally,for example, n-propylsulfinyl, 1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-Alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsuIfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.C₁-C₈-Alkylsulfinyl is additionally, for example, heptylsulfinyl,octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.C₁-C₁₀-Alkylsulfinyl is additionally, for example, nonylsulfinyl,decylsulfinyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfinyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₄-haloalkylsulfinyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₆-haloalkylsulfinyl”is a C₁-C₆-haloalkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₁₀-haloalkylsulfinyl” is a C₁-C₁₀-haloalkylgroup, as defined above, attached via a sulfinyl [S(O)] group.C₁-C₂-Haloalkylsulfinyl is, for example, S(O)CH₂F, S(O)CHF₂, S(O)CF₃,S(O)CH₂Cl, S(O)CHCl₂, S(O)CCl₃, chlorofluoromethylsulfinyl,dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,2,2,2-trichloroethylsulfinyl or S(O)C₂F₅. C₁-C₄-Haloalkylsulfinyl isadditionally, for example, 2-fluoropropylsulfinyl,3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl,2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl,2-bromopropylsulfinyl, 3-bromopropylsulfinyl,3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl,S(O)CH₂—C₂F₅, S(O)CF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylsulfinyl,1-(CH₂Cl)-2-chloroethylsulfinyl, 1-(CH₂Br)-2-bromoethylsulfinyl,4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl ornonafluorobutylsulfinyl. C₁-C₆-Haloalkylsulfinyl is additionally, forexample, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl,5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl,6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term “C₁-C₂-alkylsulfonyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₃-alkylsulfonyl” isa C₁-C₃-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. The term “C₁-C₄-alkylsulfonyl” is a C₁-C₄-alkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-alkylsulfonyl” is a C₁-C₆-alkyl group, as defined above, attachedvia a sulfonyl [S(O)₂] group. The term “C₁-C₁₀-alkylsulfonyl” is aC₁-C₁₀-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. C₁-C₂-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.C₁-C₃-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or1-methylethylsulfonyl (isopropylsulfonyl). C₁-C₄-Alkylsulfonyl isadditionally, for example, butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-Alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.C₁-C₈-Alkylsulfonyl is additionally, for example, heptylsulfonyl,octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.C₁-C₁₀-Alkylsulfonyl is additionally, for example, nonylsulfonyl,decylsulfonyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfonyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₃-haloalkylsulfonyl” is a C₁-C₃-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₄-haloalkylsulfonyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-haloalkylsulfonyl” is a C₁-C₆-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁₀-haloalkylsulfonyl” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. C₁-C₂-Haloalkylsulfonylis, for example, S(O)₂CH₂F, S(O)₂CHF₂, S(O)₂CF₃, S(O)₂CH₂Cl, S(O)₂CHCl₂,S(O)₂CCl₃, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl,2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl orS(O)₂C₂F₅. C₁-C₃-Haloalkylsulfonyl is additionally, for example,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, S(O)₂CH₂—C₂F₅, S(O)₂CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfonyl, 1-(CH₂Cl)-2-chloroethylsulfonylor1-(CH₂Br)-2-bromoethylsulfonyl. C₁-C₄-Haloalkylsulfonyl is additionally,for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C₁-C₆-Haloalkylsulfonylis additionally, for example, 5-fluoropentylsulfonyl,5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl,undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl.

The substituent “oxo” replaces a CH₂ group by a C(═O) group.

The term “C₁-C₄-alkylcarbonyl” relates to a C₁-C₄-alkyl group, asdefined above, attached via a carbonyl [C(═O)] group. Examples areacetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl,isopropylcarbonyl, n-butylcarbonyl and the like.

The term “C₁-C₄-haloalkylcarbonyl” relates to a C₁-C₄-haloalkyl group,as defined above, attached via a carbonyl [C(═O)] group. Examples aretrifluoromethylcarbonyl, 2,2,2-trifluoroethylcarbonyl and the like.

The term “aminocarbonyl” is a group —C(═O)—NH₂.

The term “C₁-C₄-alkylaminocarbonyl” is a group —C(═O)—N(H)C₁-C₄-alkyl.Examples are methylaminocarbonyl, ethylaminocarbonyl,propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and thelike.

The term “di-(C₁-C₄-alkyl)aminocarbonyl” is a group—C(═O)—N(C₁-C₄-alkyl)₂. Examples are dimethylaminocarbonyl,diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropylaminocarbonyl,diisopropylaminocarbonyl, methylpropylaminocarbonyl,methylisopropylaminocarbonyl, ethylpropylaminocarbonyl,ethylisopropylaminocarbonyl, dibutylaminocarbonyl and the like.

The remarks made below concerning preferred embodiments of the variablesof the compounds of formula I, especially with respect to theirsubstituents A, A¹, A², X¹, B¹, B², B³, B⁴, B⁵, R^(g1), R^(g2), R¹, R²,R^(3a), R^(3b), R⁵¹, R⁵², R⁶¹, R⁶², R^(7a), R^(7b), R⁸¹, R⁸², R⁹¹, R⁹²,R^(101a), R^(101b), R^(101c), R^(101d), R^(102a), R^(102b), R^(102c),R^(102d), R^(112a), R^(112b), R^(14a), R^(14b), R¹⁶, k, and p, thefeatures of the use and method according to the invention and of thecomposition of the invention are valid both on their own and, inparticular, in every possible combination with each other.In the heterocyclic rings, R¹⁶ may be bound to a carbon ring atom or toa secondary nitrogen ring atom (in the latter case thus replacing thehydrogen atom shown in the above E-x rings). If R¹⁶ is bound to anitrogen ring atom, R¹⁶ is preferably not halogen, cyano, nitro or aradical bound via O or S, such as alkoxy, haloalkoxy, alkylthio,haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl orhaloalkylsulfonyl.In one embodiment of the invention X¹ is O. In another embodiment of theinvention X¹ is CH₂. Preferably, however, X¹ is O.W is preferably O.

In one embodiment of the invention (embodiment 1) A is A¹, where W, R⁵¹and R⁶¹ have one of the above general, or, in particular, one of thebelow (for W: above) preferred meanings.

In a preferred embodiment of embodiment 1 (embodiment 1a), R⁵¹ ishydrogen.

In another preferred embodiment of embodiment 1 (embodiment 1b)

-   R⁶¹ is selected from the group consisting of C₁-C₂-alkyl which    carries one radical R⁸¹, C₁-C₂-haloalkyl which carries one radical    R⁸¹, C₃-C₆-cycloalkyl which may be substituted by 1 or 2 CN    substituents; C₃-C₆-halocycloalkyl; and a heterocyclic ring selected    from rings E-44 and E-53; where    -   R⁸¹ is selected from the group consisting of C₃-C₆-cycloalkyl        which optionally carries a CN or C₁-haloalkyl substituent,        C₃-C₆-halocycloalkyl, —C(═O)N(R^(101c))R^(101d), and a        heterocyclic ring selected from rings E-1 to E-63 as defined        above and in particular from rings E-1 to E-9; where        -   R^(101c) is selected from the group consisting of hydrogen            and C₁-C₄-alkyl; and        -   R^(101d) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl and C₁-C₆-haloalkyl.

More particularly (embodiment 1c)

-   R⁶¹ is selected from the group consisting of C₁-C₂-alkyl which    carries one radical R⁸¹, C₃-C₆-cycloalkyl and a heterocyclic ring    selected from rings E-44 and E-53; where    -   R⁸¹ is selected from the group consisting of C₃-C₆-cycloalkyl,        —C(═O)N(R^(101c))R^(101d), and a heterocyclic ring selected from        rings E-1 to E-9; where        -   R^(101c) is hydrogen; and        -   R^(101d) is selected from the group consisting of            C₁-C₆-alkyl and C₁-C₆-haloalkyl.

In another particular embodiment of embodiment 1 (embodiment 1d)

-   R⁶¹ is selected from C₁-C₄-alkyl carrying one substituent R⁸¹, ring    E-44-1 and ring E-53-1

-   -   wherein    -   n is 0, 1 or 2; and    -   R^(16a) is selected from the group consisting of hydrogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₂-C₄-alkynyl, C₂-C₄-haloalkynyl and CH₂—(C₃-C₆-cycloalkyl); and        in particular from hydrogen and C₁-C₄-alkyl; and

-   R⁸¹ is selected from rings E-44-1 and E-57-1

-   -   wherein    -   n is 0, 1 or 2

In a more preferred embodiment of embodiment 1d (embodiment 1e) R⁶¹ isselected from methyl carrying one substituent R⁸¹ (—CH₂—R⁸¹), ringE-44-1 and ring E-53-1, where R⁸¹, ring E-44-1 and ring E-53-1 are asdefined in embodiment Id.

In a particular embodiment (embodiment 1f) R⁵¹ is hydrogen and R⁶¹ is asdefined in embodiment 1b, 1c, 1d or 1e.

In one embodiment of the invention (embodiment 2) A is A², where R^(7a),R^(7b), R⁵² and R⁶² have one of the above general, or, in particular,one of the below preferred meanings.

In a preferred embodiment of embodiment 2 (embodiment 2a), R^(7a) ishydrogen and R^(7b) is selected from hydrogen, CH₃, CF₃ and CN. In aparticular embodiment of embodiment 2a (embodiment 2aa), R^(7a) andR^(7b) are hydrogen.

In another preferred embodiment of embodiment 2 (embodiment 2b), R⁵² isselected from hydrogen and C₁-C₃-alkyl, and is in particular hydrogen.

In another preferred embodiment of embodiment 2 (embodiment 2c), R⁶² isselected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted byone radical R⁸²; C₃-C₆-cycloalkyl which optionally carries a CNsubstituent, C₃-C₆-halocycloalkyl, phenyl which is optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a heterocyclicring selected from rings of formulae E-1 to E-63 as defined above; whereR⁸² and R¹⁶ have one of the above general, or, in particular, one of thebelow preferred meanings.

R⁸² is preferably selected from CN, C₃-C₆-cycloalkyl which optionallycarries a CN or CF₃ substituent; C₃-C₆-halocycloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, phenyl, optionally substituted with 1, 2 or 3substituents R¹⁶, and a heterocyclic ring selected from rings E-1 toE-63 as defined above.

R¹⁶ in phenyl and in rings E-1 to E-63 of embodiment 2 or 2c ispreferably selected from halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In a particular embodiment of embodiment 2 (embodiment 2d),

-   R^(7a) is hydrogen;-   R^(7b) is selected from hydrogen, CH₃, CF₃ and CN;-   R⁵² is selected from hydrogen and C₁-C₃-alkyl; and-   R⁶² is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl    substituted by one radical R⁸²; C₃-C₆-cycloalkyl which optionally    carries a CN substituent; C₃-C₆-halocycloalkyl, phenyl which is    optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a    heterocyclic ring selected from rings of formulae E-1 to E-63 as    defined above; where    -   R⁸² is selected from CN, C₃-C₆-cycloalkyl which optionally        carries a CN or CF₃ substituent; C₃-C₆-halocycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, phenyl, optionally substituted with 1,        2 or 3 substituents R¹⁶; and a heterocyclic ring selected from        rings E-1 to E-63 as defined above;    -   and    -   R¹⁶ in phenyl and in rings E-1 to E-63 is selected from halogen,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

In a more particular embodiment of embodiment 2 (embodiment 2e),

-   R^(7a) and R^(7b) are hydrogen,-   R⁵² is hydrogen; and-   R⁶² is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl    substituted by one radical R⁸²; C₃-C₆-cycloalkyl which optionally    carries a CN substituent; and C₃-C₆-halocycloalkyl; where    -   R⁸² is selected from CN, C₃-C₆-cycloalkyl which optionally        carries a CN or CF₃ substituent; C₃-C₆-halocycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl and        C₁-C₆-haloalkylsulfonyl; and in particular from        C₁-C₆-alkylsulfonyl and C₁-C₆-haloalkylsulfonyl.

In a specific embodiment of embodiment 2 (embodiment 2f),

-   R^(7a) and R^(7b) are hydrogen,-   R⁵² is hydrogen; and-   R⁶² is selected from C₁-C₆-alkyl, C₁-C₄-alkyl substituted by one    radical R⁸²; and C₃-C₆-cycloalkyl; where    -   R⁸² is selected from C₆-alkylsulfonyl and        C₁-C₆-haloalkylsulfonyl.

Preferably, B² is CR², where R² is not hydrogen, and B¹, B³, B⁴ and B⁵are CR², where R² has one of the above general, or, in particular, oneof the below preferred meanings. More preferably B¹ and B⁵ are CH, B² isCR², where R² is not hydrogen, and B³ and B⁴ are CR², where R² has oneof the above general, or, in particular, one of the below preferredmeanings.

Preferably R² is selected from hydrogen, F, Cl, Br, OCF₃ and CF₃, and inparticular from hydrogen, F and Cl.

In a particular embodiment (embodiment 3a), in compounds I, B² is CR²,where R² is not hydrogen, and B¹, B³, B⁴ and B⁵ are CR², where R² hasone of the above general, or, in particular, one of the above preferredmeanings; A is A¹, W is O; and R⁵¹ and R⁶¹ are as defined in any of theabove embodiments 1a, 1b, 1c, 1d, 1e or 1f.

In a more particular embodiment (embodiment 3b), in compounds I, B¹ andB⁵ are CH, B² is CR², where R² is not hydrogen, and B³ and B⁴ are CR²,where R² has one of the above general, or, in particular, one of theabove preferred meanings; A is A¹, W is O; and R⁵¹ and R⁶¹ are asdefined in any of the above embodiments 1a, 1 b, 1c, 1d, 1e or 1f.

In another particular embodiment (embodiment 3c), in compounds I, B² isCR², where R² is not hydrogen, and B¹, B³, B⁴ and B⁵ are CR², where R²has one of the above general, or, in particular, one of the abovepreferred meanings; A is A², and R^(7a), R^(7b), R⁵² and R⁶² are asdefined in any of the above embodiments 2a, 2aa, 2b, 2c, 2d, 2e or 2f.

In another more particular embodiment (embodiment 3d), in compounds I,B¹ and B⁵ are CH, B² is CR², where R² is not hydrogen, and B³ and B⁴ areCR², where R² has one of the above general, or, in particular, one ofthe above preferred meanings; A is A², and R^(7a), R^(7b), R⁵² and R⁶²are as defined in any of the above embodiments 2a, 2aa, 2b, 2c, 2d, 2eor 2f.

Preferably (embodiment 4) R^(g1) and R^(g2) form together a bridginggroup selected from —CH₂CH₂O—, —OCH₂CH₂—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—,—SCH₂CH₂—, —CH₂SCH₂—, —SCH₂S—, —OCH₂S—, —SCH₂O—, —CH₂CH₂S(O)—,—S(O)CH₂CH₂—, —CH₂S(O)CH₂—, —CH₂CH₂S(O)₂—, —S(O)₂CH₂CH₂—, —CH₂S(O)₂CH₂—,—CH₂CH₂CH₂O— and —OCH₂CH₂CH₂—, and in particular from —CH₂CH₂O—,—OCH₂CH₂—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —SCH₂CH₂—, —CH₂SCH₂—, —SCH₂S—,—OCH₂S— and —SCH₂O—. More preferably (embodiment 4a) R^(g1) and R^(g2)form together a bridging group selected from —CH₂CH₂O—, —OCH₂CH₂—,—CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S— and —SCH₂CH₂—, and in particular form—CH₂CH₂O— (so that 0 is bound in the position of R^(g2)). Alternatively,in a more preferred embodiment (embodiment 4b), R^(g1) and R^(g2) formtogether a bridging group selected from —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—,—CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂S(O)—, —CH₂S(O)CH₂—, —CH₂CH₂S(O)₂—,—CH₂S(O)₂CH₂— and —CH₂CH₂CH₂O—. The C, S or O atom on the right part ofthe bridging group is bound in position of R^(g2) and the C, S or O atomon the left part in position of R^(g1). For instance, in —CH₂CH₂O—, O isbound in position of R^(g2).

In a particular embodiment (embodiment 4c) R^(g1) and R^(g2) formtogether a bridging group selected from —CH₂CH₂O—, —OCH₂CH₂—, —CH₂OCH₂—,—OCH₂O—, —CH₂CH₂S—, —SCH₂CH₂—, —CH₂SCH₂—, —SCH₂S—, —OCH₂S—, —SCH₂O—,—CH₂CH₂S(O)—, —S(O)CH₂CH₂—, —CH₂S(O)CH₂—, —CH₂CH₂S(O)₂—, —S(O)₂CH₂CH₂—,—CH₂S(O)₂CH₂—, —CH₂CH₂CH₂O— and —OCH₂CH₂CH₂—, and B¹, B², B³, B⁴, B⁵,A¹, A², W, R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵² and R⁶² are as defined in anyof embodiments 1a, 1b, 1c, 1d, 1e, 1f, 2a, 2aa, 2b, 2c, 2d, 2e, 2f, 3a,3b, 3c or 3d.

In a more particular embodiment (embodiment 4d) R^(g1) and R^(g2) formtogether a bridging group selected from —CH₂CH₂O—, —OCH₂CH₂—, —CH₂OCH₂—,—OCH₂O—, —CH₂CH₂S—, —SCH₂CH₂—, —CH₂SCH₂—, —SCH₂S—, —OCH₂S— and —SCH₂O—,and B¹, B², B³, B⁴, B⁵, A¹, A², W, R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵² and R⁶²are as defined in any embodiments 1a, 1b, 1c, 1d, 1e, 1f, 2a, 2aa, 2b,2c, 2d, 2e, 2f, 3a, 3b, 3c or 3d.

In a more particular embodiment (embodiment 4e) R^(g1) and R^(g2) formtogether a bridging group selected from —CH₂CH₂O—, —OCH₂CH₂—, —CH₂OCH₂—,—OCH₂O—, —CH₂CH₂S— and —SCH₂CH₂—, and B¹, B², B³, B⁴, B⁵, A¹, A², W,R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵² and R⁶² are as defined in any embodiments1a, 1b, 1c, 1d, 1e, 1f, 2a, 2aa, 2b, 2c, 2d, 2e, 2f, 3a, 3b, 3c or 3d.

In another more particular embodiment (embodiment 4f) R^(g1) and R^(g2)form together a bridging group selected from —CH₂CH₂O—, —CH₂OCH₂—,—OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂S(O)—, —CH₂S(O)CH₂—,—CH₂CH₂S(O)₂—, —CH₂S(O)₂CH₂— and —CH₂CH₂CH₂O—, and B¹, B², B³, B⁴, B⁵,A¹, A², W, R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵² and R⁶² are as defined in anyembodiments 1a, 1b, 1c, 1d, 1e, 1f, 2a, 2aa, 2b, 2c, 2d, 2e, 2f, 3a, 3b,3c or 3d.

In a very particular embodiment (embodiment 4g) R^(g1) and R^(g2) formtogether —CH₂CH₂O— (so that O is bound in the position of R^(g2)), andB¹, B², B³, B⁴, B⁵, A¹, A², W, R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵² and R⁶² areas defined in any embodiments 1a, 1b, 1c, 1d, 1e, 1f, 2a, 2aa, 2b, 2c,2d, 2e, 2f, 3a, 3b, 3c or 3d.

Preferably, R¹ is CF₃. In particular (embodiment 5) R¹ is CF₃ and B¹,B², B³, B⁴, B⁵, A¹, A², W, R⁵¹, R⁶¹, R^(7a), R^(7b), R⁵², R⁶², R^(g1)and R^(g2) are as defined in any embodiments 1a, 1b, 1c, 1d, 1e, 1f, 2a,2aa, 2b, 2c, 2d, 2e, 2f, 3a, 3b, 3c, 3d, 4, 4a, 4b, 4c, 4d, 4e, 4f or4g.

Preferably, R^(3a) and R^(3b) are independently of each other selectedfrom hydrogen and fluorine, and are in particular hydrogen. Inparticular (embodiment 6) R^(3a) and R^(3b) are independently of eachother selected from hydrogen and fluorine, and are in particularhydrogen, and B¹, B², B³, B⁴, B⁵, A¹, A², W, R¹, R⁵¹, R⁶¹, R^(7a),R^(7b), R⁵², R⁶², R^(g1) and R^(g2) are as defined in any embodiments1a, 1b, 1c, Id, 1e, 1f, 2a, 2aa, 2b, 2c, 2d, 2e, 2f, 3a, 3b, 3c, 3d, 4,4a, 4b, 4c, 4d, 4e, 4f, 4g or 5.

In a particular embodiment, the compound of formula I is a compound offormula IA or an N-oxide, a stereoisomer or an agriculturally orveterinarily acceptable salt thereof

wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is CH₂—C(O)—N(H)—R^(101d), wherein    -   R^(101d) is selected from the group consisting of C₁-C₄-alkyl,        C₂-C₄-alkyl substituted with 1 or 2 fluorine atoms,        C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl and C₃-C₆-cycloalkylmethyl.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is —CH₂—R⁸¹, wherein    -   R⁸¹ is selected from rings E-5, E-6, E-7, E-19, E-25, E-27, E-44        and E-57 as defined above, where the rings E-5, E-6, E-7, E-19,        E-27, E-44 and E-57 are unsubstituted (k is 0) or carry 1 or 2        substituents R¹⁶ (k is 1 or 2) and where ring E-25 carries one        R¹⁶ substituent on the nitrogen atom in the 1-position and        optionally carries 1 or 2 further substituents R¹⁶;        -   and is in particular selected from rings E-5, E-6, E-7,            E-19, E-25, E-27, E-44-1 and E-57-1, where the rings E-5,            E-6, E-7, E-19 and E-27 are unsubstituted (k is 0) or carry            1 or 2 substituents R¹⁶ (k is 1 or 2) and where ring E-25            carries one R¹⁶ substituent on the nitrogen atom in the            1-position and optionally carries 1 or 2 further            substituents R¹⁶;        -   where in the above rings        -   each R¹⁶ is independently selected from halogen, cyano,            nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy,            C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,            C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl,            C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl,            C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl and            C₂-C₃-alkynyl;            -   where however R¹⁶ bound in the 1-position of E-25 is not                halogen, cyano, nitro, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy,                C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,                C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl,                C₁-C₂-alkylsulfonyl or C₁-C₂-haloalkylsulfonyl.

In yet another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is selected from rings E-2, E-4, E-6, E-8, E-9, E-44, E-46, E-51    and E-53 as defined above, where the rings E-2, E-4, E-6, E-8, E-9,    E-44, E-46 and E-53 are unsubstituted (k is 0) or carry 1 or 2    substituents R¹⁶ (k is 1 or 2), wherein    -   each R¹⁶ is independently selected from halogen, cyano, nitro,        C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy,        C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl,        C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl,        C₁-C₂-haloalkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl,        C₂-C₃-alkenyl and C₂-C₃-alkynyl; and    -   where ring E-51 is a ring of formula E-51-1

-   -   -   wherein        -   R^(16b) is selected from the group consisting of hydrogen,            C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₃-C₄-cycloalkyl,            C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkynyl.

In this embodiment, rings E-44 and E-53 are preferably rings E-44-1 andE-53-1 as defined above.

In yet another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2C) is Cl; and-   R⁶¹ is selected from C₂-C₄-alkyl which may be substituted with 1 or    2 fluorine atoms, cyclopropyl, C₃-C₅-halocycloalkyl,    CH₂—(C₃-C₅-halocycloalkyl), CH₂-(1-cyano-(C₃-C₅-cycloalkyl)),    C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN and —CH═NOR⁹¹, wherein R⁹¹ is    selected from C₁-C₃-alkyl and C₁-C₃-haloalkyl.

In yet another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)R^(14b) and rings E-1 and        E-7 as defined above, where        -   R^(14b) is selected from C₁-C₃-alkyl, C₁-C₃-haloalkyl and            cyclopropyl; and where in rings E-1 and E-7        -   k is 0, 1 or 2; and        -   each R¹⁶ is independently selected from halogen, cyano,            nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy,            C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,            C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl,            C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl,            C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl,            C₂-C₃-alkynyl.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is CH₂—C(O)—N(H)—R^(101d), wherein    -   R^(101d) is selected from the group consisting of        2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl,        cyclopropylmethyl, allyl and propargyl.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is —CH₂—R⁸¹, wherein    -   R⁸¹ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is selected from rings E-9, E-44, E-46 and E-53; where in rings    E-9, E-44 and E-46 k is 0; and is in particular selected from rings    E-9, E-44, E-46 and E-53-1 with R^(16a)═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings E-9, E-44 and E-46 k is 0.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another particular embodiment, the compound of formula I is acompound of formula IA as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB or an N-oxide, a stereoisomer or anagriculturally or veterinarily acceptable salt thereof

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is CH₂—C(O)—N(H)—R^(101d), wherein    -   R^(101d) is selected from the group consisting of        2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl,        cyclopropylmethyl, allyl and propargyl.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is —CH₂—R⁸¹, wherein    -   R⁸¹ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is selected from rings E-9, E-44, E-46 and E-53; where in rings    E-9, E-44 and E-46 k is 0; and is in particular selected from rings    E-9, E-44, E-46 and E-53-1 with R^(16a)═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings E-9, E-44 and E-46 k is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl; and-   R⁶¹ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is CH₂—C(O)—N(H)—R^(101d), wherein    -   R^(101d) is selected from the group consisting of        2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl,        cyclopropylmethyl, allyl and propargyl.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2C) is Cl; and-   R⁶¹ is —CH₂—R⁸¹, wherein    -   R⁸¹ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is selected from rings E-9, E-44, E-46 and E-53; where in rings    E-9, E-44 and E-46 k is 0; and is in particular selected from rings    E-9, E-44, E-46 and E-53-1 with R^(16a)═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings E-9, E-44 and E-46 k is 0.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another particular embodiment, the compound of formula I is acompound of formula IB as defined above or an N-oxide, a stereoisomer oran agriculturally or veterinarily acceptable salt thereof, wherein

-   R^(g1) and R^(g2) have one of the above general or, in particular,    one of the above preferred meanings;-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl; and-   R⁶¹ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

The invention further relates to compounds of formula II

wherein B¹, B², B³, B⁴, B⁵, X¹, R¹, R^(3a), R^(3b), R^(g1) and R^(g2)have one of the above general or preferred meanings; and

-   Y is selected from hydrogen and OR¹⁷, where    -   R¹⁷ is selected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Compounds II have biological activity, too, but are especially useful asintermediate compounds in the preparation of compounds I wherein A isA¹. Thus, the invention also relates to intermediate compounds II and tothe use of such compounds in the preparation of compounds I.

Examples of preferred compounds are compounds of the following formulaeIa.1 to Ia.40, where R^(2a), R^(2b) and R^(2c) have one of the generalor preferred meanings given above for R² and the other variables haveone of the general or preferred meanings given above. Examples ofpreferred compounds are the individual compounds compiled in the tables1 to 3400 below. Moreover, the meanings mentioned below for theindividual variables in the tables are per se, independently of thecombination in which they are mentioned, a particularly preferredembodiment of the substituents in question.

Table 1

Compounds of the formula Ia.1 in which R⁶¹ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 2

Compounds of the formula Ia.1 in which R⁶¹ is methyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3

Compounds of the formula Ia.1 in which R⁶¹ is ethyl, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 4

Compounds of the formula Ia.1 in which R⁶¹ is n-propyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 5

Compounds of the formula Ia.1 in which R⁶¹ is n-butyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 6

Compounds of the formula Ia.1 in which R⁶¹ is sec-butyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 7

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CN, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 8

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CH═CH₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 9

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CH═CH—CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 10

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂C≡CH, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 11

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂OCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 12

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂OCH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 13

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂OCF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 14

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂OCH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 15

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂SCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 16

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂S(O)CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 17

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂S(O)₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 18

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂SCH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 19

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂S(O)CH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 20

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂S(O)₂CH₂CH₃, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 21

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂SCF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 22

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂CH₂S(O)CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 23

Compounds of the formula Ia.1 in which R⁶¹ is CH₂CHF₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 24

Compounds of the formula Ia.1 in which R⁶¹ is CH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 25

Compounds of the formula Ia.1 in which R⁶¹ is CH₂CH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 26

Compounds of the formula Ia.1 in which R⁶¹ is CH₂CH₂CHF₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 27

Compounds of the formula Ia.1 in which R⁶¹ is cyclopropyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 28

Compounds of the formula Ia.1 in which R⁶¹ is 1-cyano-cyclopropyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 29

Compounds of the formula Ia.1 in which R⁶¹ is 2-fluorocyclopropyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 30

Compounds of the formula Ia.1 in which R⁶¹ is 2,2-difluorocyclopropyl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 31

Compounds of the formula Ia.1 in which R⁶¹ is cyclobutyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 32

Compounds of the formula Ia.1 in which R⁶¹ is 1-cyano-cyclobutyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 33

Compounds of the formula Ia.1 in which R⁶¹ is 3,3-difluorocyclobutyl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 34

Compounds of the formula Ia.1 in which R⁶¹ is cyclopentyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 35

Compounds of the formula Ia.1 in which R⁶¹ is 1-cyano-cyclopentyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 36

Compounds of the formula Ia.1 in which R⁶¹ is cyclohexyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 37

Compounds of the formula Ia.1 in which R⁶¹ is 1-cyano-cyclohexyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 38

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-cyclopropyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 39

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-cyano-cyclopropyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 40

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-fluoro-cyclopropyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 41

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-trifluoromethyl-cyclopropyl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 42

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-difluoromethyl-cyclopropyl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 43

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2-difluorocyclopropyl), and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 44

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2-dichlorocyclopropyl), and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 45

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2-dibromocyclopropyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 46

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-cyclobutyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 47

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1-cyano-cyclobutyl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 48

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-fluoro-cyclobutyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 49

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2-difluorocyclobutyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 50

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(3,3-difluorocyclobutyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 51

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2,3,3-tetrafluorocyclobutyl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 52

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-cyclopentyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 53

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(-1-fluoro-cyclopentyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 54

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-cyano-cyclopentyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 55

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(2,2-difluorocyclopentyl), and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 56

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(3,3-difluorocyclopentyl), and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 57

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-cyclohexyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 58

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1-fluorocyclohexyl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 59

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1-cyanocyclohexyl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 60

Compounds of the formula Ia.1 in which R⁶¹ is thietan-3-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 61

Compounds of the formula Ia.1 in which R⁶¹ is 1-oxo-thietan-3-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 62

Compounds of the formula Ia.1 in which R⁶¹ is 1,1-dioxo-thietan-3-yl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 63

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-thietan-3-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 64

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1-oxo-thietan-3-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 65

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,1-dioxo-thietan-3-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 66

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-thietan-2-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 67

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1-oxo-thietan-2-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 68

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,1-dioxo-thietan-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 69

Compounds of the formula Ia.1 in which R⁶¹ is tetrahydrothiophen-3-yl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 70

Compounds of the formula Ia.1 in which R⁶¹ is1-oxo-tetrahydrothiophen-3-yl, and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 71

Compounds of the formula Ia.1 in which R⁶¹ is1,1-dioxo-tetrahydrothiophen-3-yl, and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 72

Compounds of the formula Ia.1 in which R⁶¹ is phenyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 73

Compounds of the formula Ia.1 in which R⁶¹ is 2-fluorophenyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 74

Compounds of the formula Ia.1 in which R⁶¹ is pyridin-2-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 75

Compounds of the formula Ia.1 in which R⁶¹ is pyridin-3-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 76

Compounds of the formula Ia.1 in which R⁶¹ is pyridin-4-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 77

Compounds of the formula Ia.1 in which R⁶¹ is pyrimidin-2-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 78

Compounds of the formula Ia.1 in which R⁶¹ is pyrimidin-4-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 79

Compounds of the formula Ia.1 in which R⁶¹ is pyrimidin-5-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 80

Compounds of the formula Ia.1 in which R⁶¹ is oxetan-3-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 81

Compounds of the formula Ia.1 in which R⁶¹ is tetrahydrofuran-2-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 82

Compounds of the formula Ia.1 in which R⁶¹ is tetrahydrofuran-3-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 83

Compounds of the formula Ia.1 in which R⁶¹ is 2-oxotetrahydrofuran-3-yl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 84

Compounds of the formula Ia.1 in which R⁶¹ is1-ethyl-2-oxo-pyrrolidin-3-yl, and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 85

Compounds of the formula Ia.1 in which R⁶¹ is 2-oxopyrrolidin-3-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 86

Compounds of the formula Ia.1 in which R⁶¹ is1-methyl-2-oxopyrrolidin-3-yl, and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 87

Compounds of the formula Ia.1 in which R⁶¹ is2-oxo-1-(2,2,2-trifluoroethyl)-pyrrolidin-3-yl, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 88

Compounds of the formula Ia.1 in which R⁶¹ is 3-oxo-isoxazolidin-4-yl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 89

Compounds of the formula Ia.1 in which R⁶¹ is2-methyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 90

Compounds of the formula Ia.1 in which R⁶¹ is2-ethyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 91

Compounds of the formula Ia.1 in which R⁶¹ is2-propyl-3-oxo-isoxazolidin-4-yl, and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 92

Compounds of the formula Ia.1 in which R⁶¹ is2-(2-fluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 93

Compounds of the formula Ia.1 in which R⁶¹ is2-(2,2-difluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 94

Compounds of the formula Ia.1 in which R⁶¹ is2-(2,2,2-trifluoroethyl)-3-oxo-isoxazolidin-4-yl, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 95

Compounds of the formula Ia.1 in which R⁶¹ is —NH-pyridin-2-yl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 96

Compounds of the formula Ia.1 in which R⁶¹ is —N(CH₃)-pyridin-2-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 97

Compounds of the formula Ia.1 in which R⁶¹ is —NH-pyrimidin-2-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 98

Compounds of the formula Ia.1 in which R⁶¹ is —NH-pyrimidin-4-yl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 99

Compounds of the formula Ia.1 in which R⁶¹ is —N(CH₃)-pyrimidin-2-yl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 100

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 101

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 102

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 103

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CH₂CH₃, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 104

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CH₂F, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 105

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CHF₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 106

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 107

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH-cyclopropyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 108

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CN, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 109

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂CH═CH₂, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 110

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂C≡CH, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 111

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂—CONH—CH₂-cyclopropyl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 112

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂—CONH—CH₂-(1-cyano-cyclopropyl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 113

Compounds of the formula Ia.1 in which R⁶¹ is benzyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 114

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyridin-2-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 115

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyridin-3-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 116

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyridin-4-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 117

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyrimidin-2-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 118

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyrimidin-4-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 119

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyrimidin-5-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 120

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyridazin-3-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 121

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyridazin-4-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 122

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(pyrazin-2-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 123

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-methylpyrazol-3-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 124

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(thiazol-2-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 125

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(thiazol-4-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 126

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,3,4-thiadiazol-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 127

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,2,4-thiadiazol-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 128

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(isothiazol-3-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 129

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(oxazol-2-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 130

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(oxazol-4-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 131

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,3,4-oxadiazol-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 132

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1,2,4-oxadiazol-3-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 133

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(isoxazol-3-yl), andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 134

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(1-methyl-1,2,4-triazol-3-yl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 135

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(4-methyl-1,2,4-triazol-3-yl), and the combination of R^(2a),R^(2b) and R^(2c) for a compound corresponds in each case to one row ofTable A

Table 136

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(tetrahydrofuran-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 137

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂-(tetrahydrofuran-3-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 138

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1,3-dioxolan-2-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 139

Compounds of the formula Ia.1 in which R⁶¹ is—CH₂CH₂-(1,3-dioxolan-2-yl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 140

Compounds of the formula Ia.1 in which R⁶¹ is —CH₂-(1,3-dioxan-2-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 141

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 142

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 143

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 144

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂CHF₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 145

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂CN, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 146

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂—CH═CH₂, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 147

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂—CH≡CH, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 148

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH-cyclopropyl, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 149

Compounds of the formula Ia.1 in which R⁶¹ is —NHCO—NH—CH₂-cyclopropyl,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 150

Compounds of the formula Ia.1 in which R⁶¹ is—NHCO—NH—CH₂-(1-cyanocyclopropyl), and the combination of R^(2a), R^(2b)and R^(2c) for a compound corresponds in each case to one row of Table A

Table 151

Compounds of the formula Ia.1 in which R⁶¹ is —CH═NOCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 152

Compounds of the formula Ia.1 in which R⁶¹ is —CH═NOCH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 153

Compounds of the formula Ia.1 in which R⁶¹ is —CH═NOCH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 154

Compounds of the formula Ia.1 in which R⁶¹ is —CH═NOCH₂CH═CH₂, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 155

Compounds of the formula Ia.1 in which R⁶¹ is —CH═NOCH₂C≡CH, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Tables 156 to 310

Compounds of the formula Ia.2 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 311 to 465

Compounds of the formula Ia.3 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 466 to 620

Compounds of the formula Ia.4 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 621 to 775

Compounds of the formula Ia.5 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 776 to 930

Compounds of the formula Ia.6 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 931 to 1085

Compounds of the formula Ia.7 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1086 to 1240

Compounds of the formula Ia.8 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1241 to 1395

Compounds of the formula Ia.9 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1396 to 1550

Compounds of the formula Ia.10 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1551 to 1705

Compounds of the formula Ia.11 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1706 to 1860

Compounds of the formula Ia.12 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 1861 to 2015

Compounds of the formula Ia.13 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2016 to 2170

Compounds of the formula Ia.14 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2171 to 2325

Compounds of the formula Ia.15 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2326 to 2480

Compounds of the formula Ia.16 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2481 to 2635

Compounds of the formula Ia.17 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2636 to 2790

Compounds of the formula Ia.18 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2791 to 2945

Compounds of the formula Ia.19 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 2946 to 3100

Compounds of the formula Ia.20 in which R⁶¹ is as defined in tables 1 to155, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 3101

Compounds of the formula Ia.21 in which R⁶² is methyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3102

Compounds of the formula Ia.21 in which R⁶² is ethyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3103

Compounds of the formula Ia.21 in which R⁶² is n-propyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3104

Compounds of the formula Ia.21 in which R⁶² is cyclpropyl, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3105

Compounds of the formula Ia.21 in which R⁶² is —CH₂CF₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3106

Compounds of the formula Ia.21 in which R⁶² is —CH₂SCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3107

Compounds of the formula Ia.21 in which R⁶² is —CH₂SCH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3108

Compounds of the formula Ia.21 in which R⁶² is —CH₂S(O)CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3109

Compounds of the formula Ia.21 in which R⁶² is —CH₂S(O)CH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3110

Compounds of the formula Ia.21 in which R⁶² is —CH₂S(O)₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3111

Compounds of the formula Ia.21 in which R⁶² is —CH₂S(O)₂CH₂CH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3112

Compounds of the formula Ia.21 in which R⁶² is —CH₂OCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3113

Compounds of the formula Ia.21 in which R⁶² is —CH₂CH₂OCH₃, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 3114

Compounds of the formula Ia.21 in which R⁶² is—CH₂-(2-tetrahydrofuranyl), and the combination of R^(2a), R^(2b) andR^(2c) for a compound corresponds in each case to one row of Table A

Table 3115

Compounds of the formula Ia.21 in which R⁶² is —CH₂-(1,3-dioxolan-2-yl),and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3116 to 3130

Compounds of the formula Ia.22 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3131 to 3145

Compounds of the formula Ia.23 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3146 to 3160

Compounds of the formula Ia.24 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3161 to 3175

Compounds of the formula Ia.25 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3176 to 3190

Compounds of the formula Ia.26 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3191 to 3205

Compounds of the formula Ia.27 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3206 to 3220

Compounds of the formula Ia.28 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3221 to 3235

Compounds of the formula Ia.29 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3236 to 3250

Compounds of the formula Ia.30 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3251 to 3265

Compounds of the formula Ia.31 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3266 to 3280

Compounds of the formula Ia.32 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3281 to 3295

Compounds of the formula Ia.33 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3296 to 3310

Compounds of the formula Ia.34 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3311 to 3325

Compounds of the formula Ia.35 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3326 to 3340

Compounds of the formula Ia.36 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3341 to 3355

Compounds of the formula Ia.37 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3356 to 3370

Compounds of the formula Ia.38 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3371 to 3385

Compounds of the formula Ia.39 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3386 to 3400

Compounds of the formula Ia.40 in which R⁶² is as defined in tables 3101to 3115, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

TABLE A No. R^(2a) R^(2b) R^(2c) A-1 F F H A-2 F H F A-3 F F F A-4 F ClF A-5 F Br F A-6 F H Cl A-7 F H Br A-8 Cl F H A-9 Cl H Cl A-10 Cl F HA-11 Cl Cl Cl A-12 Cl F Cl A-13 Cl Br Cl A-14 Cl H Br A-15 Br F H A-16Br H Br A-17 Br F Br A-18 Br Cl Br A-19 CF₃ H H A-20 CF₃ H F A-21 CF₃ HCl A-22 CF₃ H Br A-23 CF₃ H CF₃ A-24 CF₃ F F A-25 CF₃ Cl Cl A-26 CF₃ F HA-27 OCF₃ H F A-28 OCF₃ H Cl A-29 OCF₃ F H A-30 OCF₃ H CF₃ A-31 OCF₃ H H

Among the above compounds, preference is given to compounds Ia.1, Ia.5and Ia.6, and in particular to Ia.1.

In a specific embodiment, the compounds I are selected from thecompounds specified in the examples, either as a free base or in form ofan agriculturally or veterinarily acceptable salt, an N-oxide or astereoisomer thereof.

The compounds of the formula (I) can be prepared by the methods asdescribed in the below schemes or in the synthesis descriptions of theworking examples, or by standard methods of organic chemistry. Thesubstituents, variables and indices are as defined above for formula(I), if not otherwise specified.

Compounds of formula I wherein X¹ is O and wherein R^(3b) is hydrogen(termed below as compounds I.a) can be prepared by reacting a compoundof formula 1 as shown in scheme 1 below in an imination/Michael additionreaction with hydroxylamine. A′ is A or a precursor of A. Typicalprecursors of A are a halogen atom, CN, carboxy, C(O)OR^(z1) or—OSO₂—R^(z1), where R^(z1) is C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenylwhich may be substituted by 1, 2 or 3 radicals selected fromC₁-C₄-alkyl, C₁-C₄-haloalkyl C₁-C₄-alkoxy or C₁-C₄-haloalkoxy. CompoundsI′ correspond to compounds I when A′ is A. Compounds I.a′ correspond tocompounds I.a when A′ is A. Suitable reaction conditions are described,for example, in WO 2012/158396. Suitably, hydroxylamine is used as thehydrochloride salt. The reaction is generally carried out in thepresence of a base, such as NaOH, KOH, Na₂CO₃ and the like. Suitablesolvents are aqueous, such as water or mixtures of water with polarsolvents, such as tetrahydrofuran, dioxane and lower alkanols. Ifnecessary (i.e. if A′ is a precursor of A), A′ is then converted into agroup A.

Compounds of formula I wherein X¹ is CH₂ and wherein R^(3b) is hydrogen(termed below as compounds I.b) can be prepared by first subjecting acompound of formula 1 to a Michael addition with nitromethane to 2, thenreducing the nitro group of 2 to an amino group. The resultingaminoketone reacts spontaneously to the pyrroline I.b′, as shown inscheme 2 below. Compounds I.b′ correspond to compounds I.b when A′ is A.Suitable reaction conditions are described, for example, in US2010/0298558. The Michael addition of nitromethane to 1 is carried outin the presence of a base. Suitable bases are for example alkalihydroxides and alcoholates, but preferably non-nucleophilic bases, suchas DBN or DBU, are used. Suitable solvents depend i.a. on the base used.If an alkali hydroxide is used, suitably an aqueous medium, such aswater of mixtures thereof with lower alkanols are used, while alkoxidesare used in the respective alcohol. If non-nucleophilic bases are used,polar, non-protic solvents, such as acetonitrile, tetrahydrofuran,dioxane and the like are preferred. If necessary (i.e. if A′ is aprecursor of A), A′ is then converted into a group A. Reduction of 2 iscarried out with a suitable reduction agent, such as Zn, Sn, Sn(II)salts, Fe or hydrogen-producing agents, such as ammonium formate in thepresence of Zn or Pd.

Compound 1 can be prepared in analogy to the method described inEP-A-2172462 and as shown in scheme 3 below by subjecting the ketones 3and 4 to an aldol condensation.

Compounds I wherein A is A¹ wherein W is O can be prepared by reacting acompound I′ wherein A′ is Cl, Br, I or triflate with carbon monoxide inthe presence of a palladium catalyst and an alcohol ROH, wherein R isC₁-C₄-alkyl, to a compound of formula 5. Suitable palladium catalystsare for example those described in WO 2011/161130.

This ester is then hydrolyzed to the respective carboxylic acid, whichis then reacted under standard amidation conditions with an amineNHR⁵¹R⁶¹. Hydrolyzation can be carried out under standard conditions,e.g. under acidic conditions using for example hydrochloric acid,sulfuric acid or trifluoroacetic acid, or under basic conditions usingfor example an alkali metal hydroxide, such as LiOH, NaOH or KOH.Amidation is preferably carried out by activation of the carboxylicacids with oxalylchloride [(COCl)₂] or thionylchloride (SOCl₂) to therespective acid chlorides, followed by reaction with an amine NHR⁵¹R⁶¹.Alternatively, amidation is carried out in the presence of a couplingreagent. Suitable coupling reagents (activators) are well known and arefor instance selected from carbodiimides, such as DCC(dicyclohexylcarbodiimide) and DIC (diisopropylcarbodiimide),benzotriazol derivatives, such as HATU(O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate), HBTU((O-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate)and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chlorotetrafluoroborate) and phosphonium-derived activators, such as BOP((benzotriazol-1-yloxy)-tris(dimethyl-amino)phosphoniumhexafluorophosphate), Py-BOP((benzotriazol-1-yloxy)-tripyrrolidinphosphonium hexafluorophosphate)and Py-BrOP (bromotripyrrolidinphosphonium hexafluorophosphate).Generally, the activator is used in excess. The benzotriazol andphosphonium coupling reagents are generally used in a basic medium.

Compounds I wherein A is A¹ wherein W is S, can be prepared by reactingthe corresponding oxo-compound (W is O) with Lawesson's reagent (CAS19172-47-5), see for example Jesberger et al., Synthesis, 2003,1929-1958 and references therein. Solvents such as HMPA or THF at anelevated temperature such as 60° C. to 100° C. can be used. Preferredreaction conditions are THF at 65° C.

Compounds I wherein A is A¹ can also be prepared from compounds I′ inwhich A′ is an aldehyde group. This aldehyde group can be oxidized tocompounds I′ wherein A′ is a carboxyl group. Suitable conditions are forexample those of the Pinnick or Lindgren oxidation using a chlorite,such as sodium chlorite NaClO₂ as oxidation agent. As scavenger for thehypochlorite (HOCl) formed in the reaction, 2-methyl-2-butene orhydrogen peroxide can be used. The Pinnick or Lindgren oxidation isgenerally carried out in a water-containing solvent under slightlyacidic, buffered conditions (pH ca. 3-5; use of a hydrogen phosphate,e.g. NaH₂PO₄). Other suitable oxidation conditions are described, forexample, in WO 2011/022337. The resulting carboxylic acid can then befurther subjected to an amidation as described above to afford compoundsI wherein A is A¹ and A¹ is C(O)NR⁵¹R⁶¹.

Compounds I′ in which A′ is an aldehyde group can in turn be preparedfrom compounds I′, in which A′ is Cl, Br, I or —OSO₂—R^(z1), whereR^(z1) is as defined above, by reaction with carbon monoxide and ahydride source, such as triethylsilane, in the presence of a transitionmetal complex catalyst, preferably a palladium catalyst. Suitablereaction conditions are described, for example, in WO 2011/161130.Alternatively, compounds I′ in which A′ is an aldehyde group (CHO) canalso be obtained by reducing a compound I′ in which A′ is C(O)OR^(z1)with R^(z1)═C₁-C₄-alkyl with diisobutylaluminium hydride (DIBAL-H)either directly to the aldehyde or via the corresponding alcohol, whichis then oxidized to the aldehyde.

Compounds I wherein R^(3b) is not hydrogen can be prepared fromcompounds I.a′ or I.b′ in analogy to the methods described in WO2010/020521 by reacting these with a base, such as lithiumdiisopropylamine, followed by the addition of an electrophile, e.g. ahalogenating agent, such as 4-iodotoluene difluoride,N-fluorobenzenesulfonimide (“NFSI”), N-chlorosuccinimide (“NCS”),N-bromosuccinimide (“NBS”) or N-iodosuccinimide (“NIS”).

Compounds I wherein A is a group A², wherein R^(7a) and R^(7b) arehydrogen, can be prepared by reducing a compound I′ wherein A′ is —CHOor —C(O)OH for example with LAH (lithium aluminium hydride) or DIBAL-H(diisobutyl aluminium hydride) to a compound 6.

This is then reacted in an S_(N) reaction with an amide NHR⁵²C(O)R⁶²,or, better, with an amine NH₂R⁵². In both cases, the OH group can firstbe converted into a better leaving group, e.g. into a sulfonate (forexample mesylate, tosylate or a triflate group). In the second variant(reaction with an amine NH₂R⁵²) the resulting benzylic amine is thenreacted with an acid R⁶²—COOH or a derivative thereof, such as its acidchloride R⁶²—COCl, in an amidation reaction.

Compounds I wherein A is a group A², wherein R^(7a) is methyl orC₁-haloalkyl and R^(7b) is hydrogen, can be prepared by subjecting aketone 7

in which R corresponds to R^(7a), which is methyl or C₁-haloalkyl, to areductive amination to furnish compounds 8. Typical conditions for thereductive amination are: Reacting ketone 7 with an amine H₂NR⁵² to yieldthe corresponding imine which is reduced to amine 8 with a reducingagent reagent such as Na(CN)BH₃. The reaction from ketone 7 to amine 8may also be carried out as a one pot procedure.

The amine 8 is then reacted with an acid R⁶²—COOH or a derivativethereof, such as its acid chloride R⁶²—COCl, in an amidation reaction,as described above.

The ketone 7 is in turn obtained by reacting a compound I′ wherein A′ isan aldehyde group —CHO with a Grignard reagent R-MgHal, where Hal is Cl,Br or I, or an organolithium compound R—Li to obtain an alcohol offormula 9, which is then oxidized to a carbonyl compound of the formula7.

For obtaining compounds in which R^(7a) and R^(7b) are methyl orC₁-haloalkyl, carbonyl compounds such as 7, in which R corresponds toR^(7a) which is methyl or C₁-haloalkyl, is reacted with a Grignardreagent R^(7b)—MgHal, where Hal is Cl, Br or I, or an organolithiumcompound R^(7b)—Li, where R^(7b) is methyl or C₁-haloalkyl, to obtain analcohol of formula 10.

Alcohol 10 can then be converted into amine 11 via the correspondingazide, as described, for example, in Organic Letters, 2001, 3(20),3145-3148.

This can be converted into compounds I wherein R⁵² is different fromhydrogen, for example by standard alkylation reactions. The groupC(O)R⁶² can be introduced as described above by acylation with an acidR⁶²—COOH or a derivative thereof, such as its acid chloride R⁶²—COCl.

Compounds I wherein A is a group A², wherein R^(7a) is CN, methyl orC₁-haloalkyl and R^(7b) is hydrogen, can be prepared by converting acompound I′ wherein A′ is an aldehyde group CHO into an imine 12 byreaction with an amine derivative NH₂R, wherein R is tert-butylsulfinyl.

This imine is then reacted with a compound X—R^(7a) in an additionreaction. Suitable reagents are for example Si(CH₃)₃—CN or HCN forintroducing CN as R^(7a), or Si(CH₃)₃—CF₃ for introducing CF₃ as R^(7a),or methyl magnesium bromide (CH₃—MgBr) for introducing a methyl group asR^(7a). Suitable conditions are described, for example, in J. Am. Chem.Soc. 2009, 3850-3851 and the references cited therein or in Chemistry—AEuropean Journal 2009, 15, 11642-11659. R (tert-butylsulfinyl) can thenbe removed under acidic conditions, such as hydrochloric acid inmethanol, to yield an amino group. The group C(O)R⁶² can then beintroduced as described above by acylating this amino group with an acidR⁶²—COOH or a derivative thereof, such as its acid chloride R⁶²—COCl.

As a rule, the compounds of formula I including their stereoisomers,salts, and N-oxides, and their precursors in the synthesis process, canbe prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared byderivatization of other compounds I or the respective precursor or bycustomary modifications of the synthesis routes described. For example,in individual cases, certain compounds of formula (I) can advantageouslybe prepared from other compounds of formula (I) by derivatization, e.g.by ester hydrolysis, amidation, esterification, ether cleavage,olefination, reduction, oxidation and the like, or by customarymodifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor on silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ortrituration.

Due to their excellent activity, the compounds of the present inventionmay be used for controlling invertebrate pests.

Accordingly, the present invention also provides a method forcontrolling invertebrate pests which method comprises treating thepests, their food supply, their habitat or their breeding ground or acultivated plant, plant propagation materials (such as seed), soil,area, material or environment in which the pests are growing or maygrow, or the materials, cultivated plants, plant propagation materials(such as seed), soils, surfaces or spaces to be protected from pestattack or infestation with a pesticidally effective amount of a compoundof the present invention or a composition as defined above. Theinvention also relates to the use of a compound of the invention, of astereoisomer and/or of an agriculturally or veterinarily acceptable saltthereof for combating invertebrate pests

Preferably, the method of the invention serves for protecting plantpropagation material (such as seed) and the plant which grows therefromfrom invertebrate pest attack or infestation and comprises treating theplant propagation material (such as seed) with a pesticidally effectiveamount of a compound of the present invention as defined above or with apesticidally effective amount of an agricultural composition as definedabove and below. The method of the invention is not limited to theprotection of the “substrate” (plant, plant propagation materials, soilmaterial etc.) which has been treated according to the invention, butalso has a preventive effect, thus, for example, according protection toa plant which grows from a treated plant propagation materials (such asseed), the plant itself not having been treated.

Alternatively preferably, the method of the invention serves forprotecting plants from attack or infestation by invertebrate pests,which method comprises treating the plants with a pesticidally effectiveamount of at least one compound of the invention, a stereoisomer thereofand/or at least one agriculturally acceptable salt thereof.

In the sense of the present invention, “invertebrate pests” arepreferably selected from arthropods and nematodes, more preferably fromharmful insects, arachnids and nematodes, and even more preferably frominsects, acarids and nematodes. In the sense of the present invention,“invertebrate pests” are most preferably insects.

The invention further provides an agricultural composition for combatinginvertebrate pests, which comprises such an amount of at least onecompound according to the invention and at least one inert liquid and/orsolid agronomically acceptable carrier that has a pesticidal action and,if desired, at least one surfactant.

Such a composition may comprise a single active compound of the presentinvention or a mixture of several active compounds of the presentinvention. The composition according to the present invention maycomprise an individual isomer or mixtures of isomers or a salt as wellas individual tautomers or mixtures of tautomers.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are in particular suitable for efficientlycontrolling animal pests such as arthropods, gastropods and nematodesincluding but not limited to:

insects from the order of Lepidoptera, for example Achroia grisella,Acleris spp. such as A. fimbriana, A. gloverana, A. variana;Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A.cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A.exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophilapometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsissarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senatoria,Antheraea pernyi, Anticarsia (=Thermesia) spp. such as A. gemmatalis;Apamea spp., Aproaerema modicella, Archips spp. such as A. argyrospila,A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella,Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetismindara, Austroasca viridigrisea, Autographa gamma, Autographanigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola,Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseolaspp., Cacoecia spp. such as C. murinana, C. podana, Cactoblastiscactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora,Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii;Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. suchas C. Indicus, C. suppressalis, C. partellus, Choreutis pariana,Choristoneura spp. such as C. conflictana, C. fumiferana, C.longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis(=Pseudoplusia) spp. such as C. eriosoma, C. includens; Cirphisunipuncta, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocismedinals, Cnephasia spp., Cochylis hospes, Coleophora spp., Coliaseurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp.,Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus,Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis,Cydia (=Carpocapsa) spp. such as C. pomonella, C. latiferreana; Dalacanoctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp. suchas D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphaniaspp. such as D. nitidalis, D. hyalinata, Diatraea grandiosella, Diatraeasaccharalis, Diphthera festiva, Earias spp. such as E. insulana, E.vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis,Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomossubsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E.elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannistiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupoeciliaambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana,Faronta albilinea, Feltia spp. such as F. subterranean; Galleriamellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G.molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedyleptaspp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea(=Heliothis zea), Heliothis spp. such as H. assulta, H. subflexa, H.virescens, Hellula spp. such as H. undalis, H. rogatalis; Helocoverpagelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hiberniadefoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homonamagnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella,Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferialycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellarialugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivoraglycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis,Leucoptera spp. such as L. coffeella, L. scitella; Leuminivoralycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattiaocto (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotisalbicosta, Loxostege spp. such as L. sticticalis, L. cereralis;Lymantria spp. such as L. dispar, L. monacha, Lyonetia clerkella,Lyonetia prunifoliella, Malacosoma spp. such as M. americanum, M.californicum, M. constrictum, M. neustria, Mamestra spp. such as M.brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M.quinquemaculata, M. sexta; Marasmia spp., Marmara spp., Marucatestulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mocisspp. such as M. lapites, M. repanda; Mocis latipes, Monochroa fragariae,Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis,Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisaanastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp.,Orthaga thyrisalis, Ostrinia spp. such as O. nubilalis; Oulema oryzae,Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris,Papilio cresphontes, Paramyelois transitella, Paranthrene regalis,Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridromasaucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala,Phryganidia californica, Phthorimaea spp. such as P. operculella;Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P.crataegella, P. issik, P. ringoniella; Pieris spp. such as P. brassicae,P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynotaspp. such as P. flavedana, P. idaeusalis, P. stultana; Platyptiliacarduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp.,Plutella maculipennis, Plutella xylostella, Pontia protodica, Praysspp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P.sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Richiaalbicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodesaegrotata, Schizura concinna, Schoenobius spp., Schreckensteiniafestaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotiasegetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotrogacerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocellana,Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. eridania, S.exigua, S. frugiperda, S. latifascia, S. littoralis, S. litura, S.omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochiSylepta derogata, Synanthedon spp. such as S. exitiosa, Teciasolanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia(=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, Thecla spp.,Thereslmima ampelophaga, Thyrinteina spp., Tildenia inconspicuella,Tinea spp. such as T. cloacella, T pellionella; Tineola bisselliella,Tortrix spp. such as T. viridana; Trichophaga tapetzella, Trichoplusiaspp. such as T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. such as U.rubigalis, U. rubigalis; Virachola spp., Yponomeuta padella, andZeiraphera canadensis;

insects from the order of Coleoptera, for example Acalymma vittatum,Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp.such as A. anxlus, A. planipennis, A. sinuatus; Agriotes spp. such as A.fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus,Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca,Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophoraspp. such as A. glabripennis; Anthonomus spp. such as A. eugenii, A.grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp.,Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A.linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda,Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis,B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne,Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella,Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchusspp. such as C. assimilils, C. napi; Chaetocnema tibialis, Cleonusmendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar,Cosmopolites spp., Costelytra zealandica, Crioceris asparagi,Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such asC. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp.,Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. suchas D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D.virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera,Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis),Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E.vigintioctomaculata; Epitrix spp. such as E. hirtipennis, E. similaris;Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbiumpsylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator,Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp.such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemusspp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne,Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L.melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea,Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodesspp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactylusspp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates,Megascelis spp., Melanotus communis, Meligethes spp. such as M. aeneus;Melolontha spp. such as M. hippocastani, M. melolontha; Metamasiushemipterus, Microtheca spp., Migdolus spp. such as M. fryanus,Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptushololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros,Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P.cochleariae; Phoracantha recurva, Phyllobius pyri, Phylloperthahorticola, Phyllophaga spp. such as P. helleri; Phyllotreta spp. such asP. chrysocephala, P. nemorum, P. striolata, P. vittula; Phylloperthahorticola, Popillia japonica, Premnotrypes spp., Psacothea hilaris,Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp.,Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp.such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R.vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorusacupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S.oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobiumpaniceum, Sternechus spp. such as S. subsignatus; Strophomorphusctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor,Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum;Trogoderma spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus;and, Zabrus spp. such as Z. tenebriodes;

insects from the order of Diptera for example Aedes spp. such as A.aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp.such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A.leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A.sinensis; Bactrocera invadens, Bibio hortulanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp.such as C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus,Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C.hominivorax; Contarinia spp. such as C. sorghicola; Cordylobiaanthropophaga, Culex spp. such as C. nigripalpus, C. pipiens, C.quinquefasciatus, C. tarsals, C. tritaeniorhynchus; Culicoides furens,Culilseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae,Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. suchas D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis,Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis;Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossinaspp. such as G. fuscipes, G. morsitans, G. palpalis, G. tachinoides;Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyiaspp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppoboscaspp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such asL. sativae, L. trifoli; Lucilia spp. such as L. caprina, L. cuprina, L.sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas M. destructor; Musca spp. such as M. autumnalis, M. domestica;Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum,Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami,Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae,P. coarctata; Phytomyza gymnostoma, Prosimulilum mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagoletis spp. such as R.ceras, R. cingulate, R. indifferens, R. mendax, R. pomonella, Rivelliaquadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simuliumvittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calcitrans;Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis;Tannia spp., Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa,and Wohlfahrtia spp.;

insects from the order of Thysanoptera for example, Baliothripsbiformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothripsamericanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F.occidentalis, F. tritici, Heliothrips spp., Hercinothrips femoralis,Kakothrips spp., Microcephalothrips abdominalis, Neohydatothripssamayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus,Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchaetothrips spp., Taeniothrips cardamoni, Taeniothrips inconsequens, Thripsspp. such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T.parvispinus, T. tabaci,

insects from the order of Hemiptera for example, Acizzia jamatonica,Acrosternum spp. such as A. hillare; Acyrthosipon spp. such as A.onobrychis, A. pisum, Adelges laricis, Adelges tsugae, Adelphocorisspp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp.,Aulacorthum solani Aleurocanthus woglumi, Aleurodes spp., Aleurodicusdisperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp.,Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp.,Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as A. craccivora,A. fabae, A. forbesi A. gossypii, A. grossulariae, A. maidiradicis, A.pomi, A. sambuci, A. schneideri, A. spiraecola, Arboridia apicalis,Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp.,Aulacaspis yasumatsui Aulacorthum solani Bactericera cockerelli(Paratrioza cockerelli), Bemisia spp. such as B. argentifolii, B. tabaci(Aleurodes tabaci), Blissus spp. such as B. leucopterus; Brachycaudusspp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola;Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae,Cacopsylla spp. such as C. fulguralls, C. pyricola (Psylla piri),Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorushorni Carneocephala fulgida, Cavelerius spp., Ceraplastes spp.,Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypiChaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii,Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimexspp. such as C. hemipterus, C. lectularius; Coccomytilus halli, Coccusspp. such as C. hesperidum, C. pseudomagnoliarum; Corythucha arcuata,Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum,Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulusspp., Dasynus piperis, Dialeurodes spp. such as D. citrifoll; Dalbulusmaidis, Diaphorina spp. such as D. cilri; Diaspis spp. such as D.bromellae; Dichelops furcatus, Diconocoris hewetti, Doralis spp.,Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp.such as D. plantaginea, D. pyri, D. radicola, Dysaulacorthumpseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedius;Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E.fabae, E. solana; Epidlaspis leperli, Eriosoma spp. such as E.lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E.integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E.impictiventris, E. servus, Fiorinia theae, Geococcus coffeae, Glycaspisbrimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp.,Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopteruspruni, Hyperomyzus lactucae, Icerya spp. such as I. purchase; Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisaspp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L.hesperus, L. lineolaris, L. pratensis; Maconellicoccus hirsutus,Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M.rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarvafimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius,Melanaphis sacchar, Melanocallis (=Tinocallis) caryaefollae, Metcafiellaspp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis,Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M.cerasi, M. nicotianae, M. persicae, M. varians, Nasonovia ribis-nigri,Neotoxoptera formosana, Neomegalotomus spp., Nephotettix spp. such as N.malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such asN. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. such as O.pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinipennis,Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. such as P.corni, P. persicae; Pemphigus spp. such as P. bursarius, P. populivenae;Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. such asP. aceris, P. gossypii; Phloeomyzus passerini, Phorodon humuli,Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp.such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P.citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallusseriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcusspp. such as P. comstocki; Psylla spp. such as P. mali; Pteromalus spp.,Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q.perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis,Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus,Rhopalosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis,R. padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp.,Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoides titanus,Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp.,Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatellafurcifera, Solubea insularis, Spissistilus festinus (=Stictocephalafestina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai,Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate,Thyanta spp. such as T. accerra, T. perditor; Tibraca spp., Tomaspisspp., Toxoptera spp. such as T. aurantii; Trialeurodes spp. such as T.abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp.,Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; andViteus vitifolii,

Insects from the order Hymenoptera for example Acanthomyops interjectus,Athalia rosae, Atta spp. such as A. capiguara, A. cephalotes, A.cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana, Bombusspp., Brachymyrmex spp., Camponotus spp. such as C. floridanus, C.pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp,Crematogaster spp., Dasymutilla occidentalis, Diprion spp.,Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formicaspp., Hoplocampa spp. such as H. minuta, H. testudinea; Iridomyrmexhumilis, Lasius spp. such as L. niger, Linepithema humile, Liometopumspp., Leptocybe invasa, Monomorium spp. such as M. pharaonis,Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechinalongicornis, Paravespula spp. such as P. germanica, P. pennsylvanica, P.vulgaris; Pheidole spp. such as P. megacephala, Pogonomyrmex spp. suchas P. barbatus, P. californicus, Polistes rubiginosa, Prenolepisimpairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus,Solenopsis spp. such as S. geminata, S. invicta, S. molesta, S.richteri, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. suchas T. melanocephalum, T. sessile; Tetramorium spp. such as T. caespitum,T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V.squamosal; Wasmannia auropunctata, Xylocopa sp;

Insects from the order Orthoptera for example Acheta domesticus,Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp.,Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. suchas G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis,Kraussaria angulifera, Locusta spp. such as L. migratoria, L. pardalina;Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M.sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleussenegalensis, Scapteriscus spp., Schistocerca spp. such as S. americana,S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerusvariegatus

Pests from the Class Arachnida for example Acari, e.g. of the familiesArgasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A.americanum, A. variegatum, A. maculatum), Argas spp. such as A.persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B.microplus, Dermacentor spp. such as D. silvarum, D. andersoni, D.variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as I.ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus,Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O.hermsi, O. turicata), Ornithonyssus bacoti, Otobius megnini, Dermanyssusgallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R.sanguineus, R. appendiculatus, Rhipicephalus evertsi), Rhizoglyphus spp;Sarcoptes spp. such as S. Scabiei; and Family Eriophyidae includingAceria spp. such as A. sheldon, A. anthocoptes, Acallitus spp; Aculopsspp. such as A. lycopersic, A. pelekassi Aculus spp. such as A.schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptrutaoleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyes sheldoniFamily Tarsonemidae including Hemitarsonemus spp., Phytonemus pallidusand Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemusspinki; Family Tenuipalpidae including Brevipalpus spp. such as B.phoenicis, Family Tetranychidae including Eotetranychus spp.,Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp.such as T. cinnabarinus, T. evansi, T. kanzawa, T, pacificus, T.phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychusspp. such as P. ulmi P. citri, Metatetranychus spp. and Oligonychus spp.such as O. pratensis, O. perseae), Vasates lycopersici; Raoiella indica,Family Carpoglyphidae including Carpoglyphus spp; Penthaleidae spp. suchas Halotydeus destructor; Family Demodicidae with species such a Demodexspp; Family Trombicidea including Trombicula spp; Family Macronyssidaeincluding Ornothonyssus spp; Family Pyemotidae including Pyemotestritici; Tyrophagus putrescentiae; Family Acaridae including Acarussiro; Family Araneida including Latrodectus mactans, Tegenaria agrestis,Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxoscelesreclusa.

Pests from the Phylum Nematoda, for example, plant parasitic nematodessuch as root-knot nematodes, Meloidogyne spp. such as M. hapla, M.incognita, M. javanica; cyst-forming nematodes, Globodera spp. such asG. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H.schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem andfoliar nematodes, Aphelenchoides spp. such as A. besseyi; Stingnematodes, Belonolaimus spp. such as B. longicaudatus; Pine nematodes,Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ringnematodes, Criconema spp.; Criconemella spp. such as C. xenoplax and C.ornata; and, Criconemoides spp. such as Criconemoides informis;Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. such as D.destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiralnematodes, Heliocotylenchus multicinctus; Sheath and sheathoidnematodes, Hemicycliophora spp. and Hemicriconemoides spp.;Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknotnematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L.elongatus; Lesion nematodes, Pratylenchus spp. such as P. brachyurus, P.neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes,Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.;Reniform nematodes, Rotylenchus spp. such as R. robustus, R. reniformis;Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T.obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stuntnematodes, Tylenchorhynchus spp. such as T. claytoni T. dubius; Citrusnematodes, Tylenchulus spp. such as T. semipenetrans; Dagger nematodes,Xiphinema spp.; and other plant parasitic nematode species.

Insects from the order Isoptera for example Calotermes flavicollis,Coptotermes spp. such as C. formosanus, C. gestro C. acinaciformis;Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons;Globitermes sulfureus, Heterotermes spp. such as H. aureus, H.longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp.,Incisitermes spp. such as I. minor, I. Snyder, Marginitermes hubbard,Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N.opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsisspp. such as Z. angusticolis, Z. nevadensis, Reticulitermes spp. such asR. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R.lucifugus, R. santonensis, R. virginicus; Termes natalensis,

Insects from the order Blattaria for example Blatta spp. such as B.orientalis, B. lateralis; Blattella spp. such as B. asahinae, B.germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. such asP. americana, P. australasiae, P. brunnea, P. fuligginosa, P. japonica;Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana,Pycnoscelus surinamensis

Insects from the order Siphonoptera for example Cediopsylla simples,Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. canis,Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans,and Nosopsyllus fasciatus,

Insects from the order Thysanura for example Lepisma saccharina,Ctenolepisma urbana, and Thermobia domestica,

Pests from the class Chilopoda for example Geophilus spp., Scutigeraspp. such as Scutigera coleoptrata;

Pests from the class Diplopoda for example Blaniulus guttulatus, Julusspp., Narceus spp.,

Pests from the class Symphyla for example Scutigerella immaculata.

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp. such asOnychiurus armatus.

Pests from the order Isopoda for example, Armadillidium vulgare, Oniscusasellus, Porcellio scaber.

Insects from the order Phthiraptera, for example Damalinia spp.,Pediculus spp. such as Pediculus humanus capitis, Pediculus humanuscorporis, Pediculus humanus humanus, Pthirus pubis, Haematopinus spp.such as Haematopinus eurysternus, Haematopinus suis; Linognathus spp.such as Linognathus vituli Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds offormula (I) include: from the Phylum Mollusca, class Bivalvia, forexample, Dreissena spp.; class Gastropoda, for example, Arion spp.,Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaeaspp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from theclass of the helminths, for example, Ancylostoma duodenale, Ancylostomaceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascarislubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomumspp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp.,Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis,Echinococcus granulosus, Echinococcus multilocularis, Enterobiusvermicularis, Faciola spp., Haemonchus spp. such as Haemonchuscontortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., LoaLoa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp.,Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomenspp., Strongyloides fuelleborni, Strongyloides stercora lis,Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis,Trichinella nativa, Trichinella britovi, Trichinella nelsoni Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichiura, Wuchereriabancrofti;

Further examples of pest species which may be controlled by compounds offormula (I) include: Anisoplia austriaca, Apamea spp., Austroascaviridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp.,Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chiloindicus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocrocimedinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp.,Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulusmaidis, Deraceras reticulatum, Diatrea saccharalis, Dichelops furcatus,Dicladispa armigera, Diloboderus spp. such as Diloboderus abderus;Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermessulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor,Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta,Leptocorsia oratorius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus,Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp.,Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocislatipes, Murgantia spp., Mythemina separata, Neocapritermes opacus,Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphuladepunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae;Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata,Procornitermes ssp, Procornitermes triacifer, Psylloides spp.,Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocorisspp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophagainnotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata,Spissistilus spp., Stalk borer, Stenchaetothrips biformis,Steneotarsonemus spinki, Sylepta derogata, Telehin licus,Trichostrongylus spp.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects, preferably sucking or piercing and chewing and biting insectssuch as insects from the genera Lepidoptera, Coleoptera and Hemiptera,in particular Lepidoptera, Coleoptera and true bugs. The compounds ofthe present invention, including their salts, stereoisomers andtautomers, are moreover useful for controlling insects of the ordersThysanoptera, Diptera (especially flies, mosquitos), Hymenoptera(especially ants) and Isoptera (especially termites.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the species to be controlled, the treated cultivatedplant or material, the climatic conditions and the specific compound Iused.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e.g. solutions, emulsions,suspensions, dusts, powders, pastes, granules, pressings, capsules, andmixtures thereof. Examples for composition types are suspensions (e.g.SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW,EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powdersor dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT),granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN),as well as gel formulations for the treatment of plant propagationmaterials such as seeds (e.g. GF). These and further compositions typesare defined in the “Catalogue of pesticide formulation types andinternational coding system”, Technical Monograph No. 2, 6^(th) Ed. May2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solidcarriers or fillers, surfactants, dispersants, emulsifiers, wetters,adjuvants, solubilizers, penetration enhancers, protective colloids,adhesion agents, thickeners, humectants, repellents, attractants,feeding stimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e.g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharide powders, e.g. cellulose, starch;fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e.g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemulsifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkyl-naphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-subsitituedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxilaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) ad 100 wt %. The activesubstance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent(e.g. cyclohexanone) ad 100 wt %. Dilution with water gives adispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in water-insoluble organic solvent (e.g.aromatic hydrocarbon) ad 100 wt %. Dilution with water gives anemulsion.iv) Emulsions (EW, EO, ES)5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into water ad100 wt % by means of an emulsifying machine and made into a homogeneousemulsion. Dilution with water gives an emulsion.v) Suspensions (SC, OD, FS)In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.vi) Water-dispersible granules and water-soluble granules (WG, SG)50-80 wt % of a compound I according to the invention are ground finelywith addition of dispersants and wetting agents (e.g. sodiumlignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e.g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andsolid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives astable dispersion or solution of the active substance.viii) Gel (GW, GF)In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and water ad 100 wt % to give a fine suspension of the active substance.Dilution with water gives a stable suspension of the active substance.ix) Microemulsion (ME)5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.x) Microcapsules (CS)An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and anisocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the formation of a polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.xi) Dustable powders (DP, DS)1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with solid carrier (e.g. finely divided kaolin) ad100 wt %.xii) Granules (GR, FG)0.5-30 wt % of a compound I according to the invention is ground finelyand associated with solid carrier (e.g. silicate) ad 100 wt %.Granulation is achieved by extrusion, spray-drying or the fluidized bed.xiii) Ultra-low volume liquids (UL)1-50 wt % of a compound I according to the invention are dissolved inorganic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xiii) may optionally comprise furtherauxiliaries, such as 0, 1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0, 1-1 wt % anti-foaming agents, and 0, 1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and in particular between 0.5 and 75%,by weight of active substance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Solutions for seed treatment (LS), Suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,on to plant propagation material, especially seeds include dressing,coating, pelleting, dusting, soaking and in-furrow application methodsof the propagation material. Preferably, compound I or the compositionsthereof, respectively, are applied on to the plant propagation materialby a method such that germination is not induced, e.g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e.g.components comprising compounds I and/or active substances from thegroups M) or F) (see below), may be mixed by the user in a spray tankand further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds I and/or active substances from thegroups M.1 to M.UN.X or F.I to F.XIII, can be applied jointly (e.g.after tank mix) or consecutively.

The following list M of pesticides, grouped and numbered according theMode of Action Classification of the Insecticide Resistance ActionCommittee (IRAC), together with which the compounds according to theinvention can be used and with which potential synergistic effects mightbe produced, is intended to illustrate the possible combinations, butnot to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors from the class of

M.1A carbamates, for example aldicarb, alanycarb, bendiocarb,benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb andtriazamate; or from the class ofM.1B organophosphates, for example acephate, azamethiphos,azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;M.2. GABA-gated chloride channel antagonists such as:M.2A cyclodiene organochlorine compounds, as for example endosulfan orchlordane; orM.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,flufiprole, pyrafluprole and pyriprole;M.3 Sodium channel modulators from the class ofM.3A pyrethroids, for example acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin,esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin,meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin,prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin,silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrinand transfluthrin; orM.3B sodium channel modulators such as DDT or methoxychlor;M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class ofM.4A neonicotinoids, for example acetamiprid, chlothianidin,cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid andthiamethoxam; or the compoundsM.4A.2:(2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide;orM4.A.3:1-[(6-Chloropyridin-3-yl)methylmethyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine;or from the class M.4B nicotine;M.5 Nicotinic acetylcholine receptor allosteric activators from theclass of spinosyns, for example spinosad or spinetoram;M.6 Chloride channel activators from the class of avermectins andmilbemycins, for example abamectin, emamectin benzoate, ivermectin,lepimectin or milbemectin;M.7 Juvenile hormone mimics, such asM.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene;or others as M.7B fenoxycarb or M.7C pyriproxyfen;M.8 miscellaneous non-specific (multi-site) inhibitors, for exampleM.8A alkyl halides as methyl bromide and other alkyl halides, orM.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8Etartar emetic;M.9 Selective homopteran feeding blockers, for exampleM.9B pymetrozine, or M.9C flonicamid;M.10 Mite growth inhibitors, for exampleM.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;M.11 Microbial disruptors of insect midgut membranes, for examplebacillus thuringiensis or bacillus sphaericus and the insecticdalproteins they produce such as bacillus thuringiensis subsp. israelensis,bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillusthuringiensis subsp. kurstaki and bacillus thuringiensis subsp.tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1 Fa, Cry2Ab,mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;M.12 Inhibitors of mitochondrial ATP synthase, for exampleM.12A diafenthiuron, orM.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatinoxide, or M.12C propargite, or M.12D tetradifon;M.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC or sulfluramid;M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, forexample nereistoxin analogues as bensultap, cartap hydrochloride,thiocyclam or thiosultap sodium;M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureasas for example bistrifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron or triflumuron;M.16 Inhibitors of the chitin biosynthesis type 1, as for examplebuprofezin;M.17 Moulting disruptors, Dipteran, as for example cyromazine;M.18 Ecdyson receptor agonists such as diacylhydrazines, for examplemethoxyfenozide, tebufenozide, halofenozide, fufenozide orchromafenozide;M.19 Octopamin receptor agonists, as for example amitraz;M.20 Mitochondrial complex III electron transport inhibitors, forexampleM.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;M.21 Mitochondrial complex I electron transport inhibitors, for exampleM.21A METI acaricides and insecticides such as fenazaquin,fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, orM.21B rotenone;M.22 Voltage-dependent sodium channel blockers, for exampleM.22A indoxacarb, or M.22B metaflumizone, or M.22B.1:2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamideor M.22B.2:N-(3-Chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic andTetramic acid derivatives, for example spirodiclofen, spiromesifen orspirotetramat;M.24 Mitochondrial complex IV electron transport inhibitors, for exampleM.24A phosphine such as aluminium phosphide, calcium phosphide,phosphine or zinc phosphide, or M.24B cyanide;M.25 Mitochondrial complex II electron transport inhibitors, such asbeta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;M.28 Ryanodine receptor-modulators from the class of diamides, as forexample flubendiamide, chlorantraniliprole (Rynaxypyr®),cyantraniliprole (Cyazypyr®), tetraniliprole or the phthalamidecompoundsM.28.1:(R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamidandM.28.2:(S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,or the compoundM.28.3:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide(proposed ISO name: cyclaniliprole), or the compoundM.28.4:methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) toM.28.51):M.28.5a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5i)N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide;M.28.5j)3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide;M.28.5k)3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide;M.28.51)N-[4-Chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide;

-   -   or a compound selected from        M.28.6: cyhalodiamide; or        M.29. insecticidal active compounds of unknown or uncertain mode        of action, as for example afidopyropen, afoxolaner,        azadirachtin, amidoflumet, benzoximate, bifenazate,        broflanilide, bromopropylate, chinomethionat, cryolite,        dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone,        fluhexafon, fluopyram, flupyradifurone, fluralaner,        metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,        pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or        the compounds        M.29.3:        11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,        or the compound        M.29.4:        3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,        or the compound        M.29.5:        1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,        or actives on basis of bacillus firmus (Votivo, I-1582); or a        compound selected from the group of M.29.6, wherein the compound        is selected from        M.29.6a) to M.29.6k):        M.29.6a)        (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;        M.29.6b)        (E/Z)—N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;        M. 29.6c)        (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;        M. 29.6d)        (E/Z)—N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;        M. 29.6e)        (E/Z)—N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;        M. 29.6f)        (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;        M. 29.6g)        (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;        M. 29.6h)        (E/Z)—N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;        M. 29.6i)        (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.);        M. 29.6j)        N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide        or of the compound        M. 29.6k)        N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N′-isopropyl-acetamidine        or        M. 29.8: fluazaindolizine; or        M. 29.9.a):        4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;        or M.29.9.b): fluxametamide; or        M. 29.10:        5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;        or a compound selected from the group of M.UN.11, wherein the        compound is selected from M.UN.11b) to M.UN.11p):        M. 29.11.b)        3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide;        M. 29.11.c)        3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;        M. 29.11.d)        N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;        M. 29.11.e)        N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;        M. 29.11.f)        4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;        M. 29.11.g)        3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;        M. 29.11.h)        2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide;        M. 29.11.i)        4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;        M. 29.11.j)        4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide;        M. 29.11.k)        N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;        M. 29.11.l)        N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;        M. 29.11.m)        N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;        M. 29.11.n)        4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;        M. 29.11.o)        4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;        M. 29.11.p)        N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;        or a compound selected from the group of M. 29.12, wherein the        compound is selected from M. 29.12a) to M. 29.12m):        M. 29.12.a)        2-(1,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine;        M. 29.12.b)        2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;        M. 29.12.c)        2-[6-[2-(3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;        M. 29.12.d)        N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide        M. 29.12.e)        N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide        M. 29.12.f)        N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide        M. 29.12.g)        N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide        M. 29.12.h)        N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide        M. 29.12.i)        N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide        M. 29.12.j)        N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide        M. 29.12.k)        N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide        M. 29.12.l)        N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide        M. 29.12.m)        N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide;        or the compounds        M. 29.14a)        1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine;        or        M. 29.14b)        1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;        or the compounds        M.29.16a)        1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        or        M.29.16b)        1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16c)        N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;        M.29.16d)        1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16e)        N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16f)        1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16g)        1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16h)        N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        M.29.16i)        1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;        or M.29.16j)        1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide,        or        M.29.17 a compound selected from the compounds M.29.17a) to        M.29.17j): M.29.17a)        N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide;        M.29.17b)        N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;        M.29.17c)        N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;        M.29.17d)        2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;        M.29.17e)        2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;        M.29.17f) methyl        2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate;        M.29.17g)        N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide;        M.29.17h)        N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide;        M.29.17i)        2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide;        M.29.17j)        N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,        or        M.29.18 a compound selected from the compounds M.29.18a) to        M.29.18d): M.29.18a)        N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide;        M.29.18b)        N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;        M.29.18c)        N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide;        M.29.18d)        N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;        or the compound        M.29.19 sarolaner, or the compound        M.29.20 lotilaner.        The commercially available compounds of the group M listed above        may be found in The Pesticide Manual, 16th Edition, C. MacBean,        British Crop Protection Council (2013) among other publications.        The online Pesticide Manual is updated regularly and is        accessible through http://bcpcdata.com/pesticide-manual.html.        Another online data base for pesticides providing the ISO common        names is http://www.alanwood.net/pesticides.        The M.4 neonicotinoid cycloxaprid is known from WO2010/069266        and WO2011/069456, and the neonicotinoid M.4A.2, sometimes also        to be named as guadipyr, is known from WO2013/003977, and the        neonicotinoid M.4A.3. (approved as paichongding in China) is        known from WO2007/101369. The metaflumizone analogue M.22B.1 is        described in CN 10171577 and the analogue M.22B.2 in        CN102126994. The phthalamides M.28.1 and M.28.2 are both known        from WO 2007/101540. The anthranilamide M.28.3 has been        described in WO2005/077934. The hydrazide compound M.28.4 has        been described in WO 2007/043677. The anthranilamides M.28.5a)        to M.28.5d) and M.28.5h) are described in WO 2007/006670,        WO2013/024009 and WO2013/024010, the anthranilamide compound        M.28.5i) is described in WO2011/085575, the compound M.28.5j) in        WO2008/134969, the compound M.28.5k) in US2011/046186 and the        compound M.28.51) in WO2012/034403. The diamide compound M.28.6        can be found in WO2012/034472.        The spiroketal-substituted cyclic ketoenol derivative M.29.3 is        known from WO2006/089633 and the biphenyl-substituted        spirocyclic ketoenol derivative M.29.4 from WO2008/067911. The        triazoylphenylsulfide M.29.5 has been described in        WO2006/043635, and biological control agents on basis of        bacillus firmus are described in WO2009/124707.        The compounds M.29.6a) to M. 29.6i) listed under M. 29.6 have        been described in WO2012/029672 and compounds M. 29.6j) and M.        29.6k) in WO2013/129688. The nematicide compound M. 29.8 is        known from WO2013/055584. The isoxazoline M.29.9.a) is described        in WO2013/050317. The isoxazoline M.29.9.b) is described in        WO2014/126208. The pyridalyl-type analogue M. 29.10 is known        from WO2010/060379. The carboxamide compounds broflanilide        and M. 29.11.b) to M. 29.11.h) can be prepared as described in        WO 2010/018714 and the carboxamide M. 29.11i) to M. 29.11.p) are        described WO2010/127926. The pyridylthiazoles M. 29.12.a) to M.        29.12.c) are known from WO2010/006713, M. 29.12.d) and and        M.29.12.e) are known from WO2012/000896 and M. 29.12.f) to M.        29.12.m) from WO2010/129497. The compounds M. 29.14a) and M.        29.14b) are known from WO2007/101369. The pyrazoles M.29.16.a)        to M.29.16h) are described in WO2010/034737, WO2012/084670, and        WO2012/143317, respectively, and the pyrazoles M.29.16i) and        M.29.16j) are described in U.S. 61/891,437. The        pyridinylindazoles M.29.17a) to M.29.17.j) are described in        WO2015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are        described in US2014/0213448. The isoxazoline M.29.19 is        described in WO2014/036056. The isoxazoline M.29.20 is known        from WO2014/090918.

Especially combinations of compounds of the invention with fiproles,neonictinoids or pyrethroids may possibly exhibit synergistic control ofstinkbugs (according to the Colby formula), in particular Euschistus,e.g. Euschistus heros.

The following list of fungicides, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them:

F.I) A) Respiration Inhibitorsinhibitors

F.I-1) Inhibitors of complex III at Qo site:

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin,dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,pyrametostrobin, pyraoxystrobin, pyribencarb,triclopyricarb/chlorodincarb, trifloxystrobin,2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methylester and 2(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-Nmethyl-acetamide; oxazolidinediones and imidazolinones: famoxadone,fenamidone;F.I-2) Inhibitors of complex II (e.g. carboxamides):carboxanilides: benodanil, benzovindiflupyr, bixafen, boscalid,carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr,isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthi-opyrad,sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide (fluxapy-roxad),N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1Hpyrazole-4-carboxamide,N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4carbox-amide, 3(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl¬indan-4-yl)pyrazole-4-carboxamide,3(trifluoromethyl)-1-methyl-N-(1,1,3-trimethyl¬indan-4-yl)pyrazole-4-carboxamide,1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyr¬azole-4-carboxamide,3-(trifluorometh¬yl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)-pyrazole-4-carboxamide,3-(difluoro¬methyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4yl)pyrazole-4-carboxamide,1,3,5-tri-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide;F.I-3) Inhibitors-Inhibitors of complex III at Qo site (e. g.strobilurins): azoxystrobin (A.1.1), coumeth¬oxy¬strobin (A.1.2),coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5),fenaminstrobin (A.1.6), fenoxy¬strobin/flufenoxystrobin (A.1.7),fluoxastro¬bin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10),meto¬minostrobin (A.1.11), orysastrobin (A.1.12), picoxy-.strobin(A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15),pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2(2-(3-(2,6-dihchlorophenyl)-1-methyl-allylidene¬aminooxy¬methyl)-phenyl)-2-methoxyimino-Nmethyl-acetamide (A.1.18), pyribencarb (A.1.19),triclopy-ricarb/chlorodin-carb (A.1.20), famoxadone (A.1.21), fenamidone(A.1.21),methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate(A.1.22), 1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.23),1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]-oxy-methyl]phenyl]-4-methyl-tetrazol-5-one(A.1.24),1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxy-methyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(A.1.25),1-[2-[[1-(4-chlorophenyl)py¬razol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one(A.1.26),1-[2-[[1-(2,4-dichloro¬phenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one(A.1.27),1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(A.1.28), 1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.29),1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]-methyl]phenyl]-4methyl-tetrazol-5-one (A.1.30), 1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1methylpyrazol-3 yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one(A.1.31), 1-methyl-4-[3-methyl-2 [[2methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one(A.1.32),1-me¬thyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]¬tetrazol-5one (A.1.33),(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.34),(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.35),(Z,2E)-5-[1-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.36),

-   -   inhibitors of complex III at Qi site: cyazofamid, (A.2.1),        amisulbrom, (A.2.2), [(3S,6S,7R,8R)-8-benz¬yl-3-[(3-acetoxy-4        methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-di¬oxonan-7-yl]        2 methylpropanoate, (A.2.3),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acet-oxymeth¬oxy)-4-methoxy-pyridine-2        carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2        methylpropanoate, (A.2.4),        [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobut¬oxycarbonyloxy-4-meth¬oxy-pyri¬dine-2        carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpro¬panoate, (A.2.5),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-ben¬zodioxol-5-ylmethoxy)-4-methoxy-pyri¬dine-2-car-bonyl]amino]-6-methyl-4,9-di¬oxo-1,5-dioxonan-7-yl]        2-methyl¬propanoate, (A.2.6);        (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6        methyl-4,9-dioxo-8-(phenylmethyl        (phenyl¬methyl)-1,5-dioxonan-7-yl 2-methylpropanoate; (A.2.7),        (3S,6S,7R,8R)-8-benzyl-3 [3        [(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl        isobutyrate (A.2.8);        F.I-4) Other respiration inhibitors (complex I, uncouplers)        diflumetorim;—inhibitors of com-plex II (e. g. carboxamides):        benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3),        boscalid (A.3.4), carboxin (A.3.5), fen¬furam (A.3.6), fluopyram        (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr        (A.3.10), isofetamid (A.3.11), iso¬pyrazam (A.3.12), mepronil        (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad        (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluz¬amide        (A.3.18), N-(4′-trifluoromethylthiobiphenyl-2-yl)-3        difluoromethyl-1-methyl-1H pyrazole-4-carboxamide (A.3.19),        N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5        fluoro-1H-pyr¬azole-4 carboxamide (A.3.20), 3        (difluoromethyl)-1-methyl-N-(1,1,3-trimethyl¬indan-4-yl)pyrazole-4-carboxamide        (A.3.21), 3        (trifluoromethyl)-1-methyl-N-(1,1,3-trimethyl¬indan-4-yl)pyrazole-4-carboxamide        (A.3.22),        1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyr¬azole-4-carboxamide        (A.3.23),        3-(trifluorometh¬yl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)¬pyrazole-4-carboxamide        (A.3.24),        1,3,5-tri¬methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-car¬boxamide        (A.3.25),        N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carbox¬amide        (A.3.26),        N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide        (A.3.27);    -   other respiration inhibitors (e. g. complex I, uncouplers):        diflumetorim (A.4.1),        (5,8-difluoro-quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine;        tecnazen; ametoctradin; silthiofam; (A.4.2); nitrophenyl        derivates: binapacryl, (A.4.3), dinobuton, (A.4.4), dinocap,        (A.4.5), fluazinam, (A.4.6); ferimzone, nitrthal-isopropyl,        (A.4.7); organometal com-pounds: fentin salts, such as        fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin        hydroxide (A.4.10); ametoctradin (A.4.11); and silthiofam        (A.4.12);        and including organometal compounds: fentin salts, such as        fentin-acetate, fentin chloride or fentin hydroxide;        F.II) B) Sterol biosynthesis inhibitors (SBI fungicides)        F.II-1)—C14 demethylase inhibitors (DMI fungicides, e.g.):        triazoles, imidazoles) triazoles: azaconazole, (B.1.1),        bitertanol, (B.1.2), bromuconazole, (B.1.3), cyproconazole,        (B.1.4), difenoconazole, (B.1.5), diniconazole, (B.1.6),        diniconazole-M, (B.1.7), epoxiconazole, (B.1.8), fenbuconazole,        (B.1.9), fluquinconazole, (B.1.10), flusilazole, (B.1.11),        flutriafol, (B.1.12), hexaconazole, (B.1.13), imibenconazole,        (B.1.14), ipconazole, (B.1.15), metconazole, (B.1.17),        myclobutanil, (B.1.18), oxpoconazole (B.1.19), paclobutrazole,        (B.1.20), penconazole, (B.1.21), propiconazole, prothioconazole,        (B.1.22), prothio¬conazole (B.1.23), simeconazole, (B.1.24),        tebuconazole, (B.1.25), tetraconazole, (B.1.26), triadimefon,        (B.1.27), triadimenol, (B.1.28), triticonazole, (B.1.29),        uniconazole, (B.1.30),        1-[rel-(2S;3R)-3-(2-chloro¬phenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5        thio¬cyanato-1H-[1,2,4]triazole,triazolo (B.1.31),        2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranyl¬methyloxi¬ranyl¬methyl]-2H        [1,2,4]triazole-3-thiol;        (B.1.32), 2-[2-chloro-4-(4-chlorophenoxy)¬phenyl]-1        (1,2,4-triazol-1-yl)pentan-2-ol (B.1.33),        1-[4-(4-chlorophenoxy)-2-(trifluoro-methyl)phenyl]-1        cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol (B.1.34),        2-[4-(4-chloro¬phenoxy)-2-(trifluorometh¬yl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.35), 2 [2        chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.36), 2 [4 (4        chloro-phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1        yl)butan-2-ol (B.1.37),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.38),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.39),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)-phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol        (B.1.40),        2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.41),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol        (B.1.51); imidazoles: imazalil, (B.1.42), pefurazoate,        oxpoconazole, (B.1.43), prochloraz, triflumizole;        (B.1.44), triflumizol (B.1.45); pyrimidines, pyridines and        piperazines: fenarimol, (B.1.46), nuarimol, (B.1.47), pyrifenox,        (B.1.48), triforine,        1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5        thiocyanato-1H-[1,2,4]triazole,        2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H        [1,2,4]triazole-3-thiol; (B.1.49),        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro¬phenyl)isoxazol-4-yl]-(3-pyridyl)methanol        (B.1.50);        F.II-2)—Delta14-reductase inhitors (Amines, e.g. morpholines,        piperidines) morpholinesinhibitors: aldimorph, (B.2.1),        dodemorph, (B.2.2), dodemorph-acetate, (B.2.3), fenpropimorph,        (B.2.4), tridemorph;        piperidines: (B.2.5), fenpropidin, (B.2.6), piperalin;        spiroketalamines: (B.2.7), spiroxamine; (B.2.8);        F.II-3)—Inhibitors of 3-keto reductase: hydroxyanilides:        fenhexamid; (B.3.1);        F.III) C) Nucleic acid synthesis inhibitors        F.III-1) RNA, DNA synthesis    -   phenylamides or acyl amino acid fungicides: benalaxyl, (C.1.1),        benalaxyl-M, (C.1.2), kiralaxyl, (C.1.3), metalaxyl, (C.1.4),        metalaxyl-M (mefenoxam, C.1.5), ofurace, (C.1.6), oxadix-yl;        (C.1.7);        isoxazoles and iosothiazolones—others: hymexazole, (C.2.1),        octhilinone;        F.III-2) DNA topisomerase inhibitors: (C.2.2), oxolinic acid;        F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase),        hydroxy (2-amino)-pyrimidines: (C.2.3), bupirimate; (C.2.4),        5-fluorocytosine (C.2.5),        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4 amine (C.2.7);        F.IV) D) Inhibitors of cell division and or cytoskeleton        F.IV-1) Tubulin—tubulin inhibitors, such as benzimidazoles and,        thiophanates: benomyl, (D1.1), carbendazim, (D1.2),        fuberidazole, (D1.3), thiabendazole, (D1.4), thiophanate-methyl;        (D1.5); triazolopyrimidines: 5-chloro-7 ((4-methylpiperidin        methyl¬piperidin-1-yl)-6-(2,4,6-trifluorophenyltrifluoro¬phenyl)-[1,2,4]triazolotri¬azolo[1,5        a]pyrimidine; (D1.6);        F.IV-2) Other—other cell division inhibitors        benzamides and phenyl acetamides: diethofencarb, (D2.1),        ethaboxam, (D2.2), pencycuron, (D2.3), fluopicolide, (D2.4),        zoxamide;        F.IV-3) Actin inhibitors: benzophenones: (D2.5), metrafenone,        (D2.6), pyriofenone; (D2.7);        F.V) E) Inhibitors of amino acid and protein synthesis        F.V-1) Methionine—methionine synthesis inhibitors        (anilino-pyrimidines) anilino-pyrimidines:): cyprodinil,        mepanipyrim, nitrapyrin, (E.1.1), mepanihpyrim (E.1.2),        pyrime-thanil; (E.1.3);        F.V-2) Protein—protein synthesis inhibitors        (anilino-pyrimidines)        antibiotics: blasticidin-S, (E.2.1), kasugamycin, (E.2.2),        kasugamycin hydrochloride-hydrate, (E.2.3), mildiomycin,        (E.2.4), streptomycin, oxytetracyclin, (E.2.5), oxytetra¬cyclin        (E.2.6), polyoxine, (E.2.7), validamycin A; (E.2.8);        F.VI)) Signal transduction inhibitors        F.VI-1)—MAP/Histidinehistidine kinase inhibitors (e.g.        anilino-pyrimidines) dicarboximides: fluoroimid, (F.1.1),        iprodione, (F.1.2), procymidone, (F.1.3), vinclozolin;        phenylpyrroles: (F.1.4), fenpiclonil, (F.1.5), fludioxonil;        (F.1.6);        F.VI-2)—G protein inhibitors: quinolines: quinoxyfen; (F.2.1);        F.VII) G) Lipid and membrane synthesis inhibitors        F.VII-1)—Phospholipid biosynthesis inhibitors        organophosphorus compounds: edifenphos, (G.1.1), iprobenfos,        pyrazophos; dithiolanes: (G.1.2), pyrazo-phos (G.1.3),        isoprothiolane; (G.1.4);        F.VII-2) Lipid—lipid peroxidation: aromatic hydrocarbons:        dicloran, (G.2.1), quintozene, (G.2.2), tecnazene, (G.2.3),        tolclofos-methyl, (G.2.4), biphenyl, (G.2.5), chloroneb,        (G.2.6), etridiazole; (G.2.7);        F.VII-3) Carboxyl acid amides (CAA fungicides)        cinnamic or mandelic acid amides-phospholipid biosynthesis and        cell wall deposition: dimethomorph, (G.3.1), flumorph,        mandiproamid, (G.3.2), mandipropamid (G.3.3), pyrimorph;        valinamide carbamates: (G.3.4), benthiavalicarb, iprovalicarb,        pyribencarb, (G.3.5), iprovali¬carb (G.3.6), valifenalate        (G.3.7) and        N-(1-(1-(4-cyano-phenyl)ethanesulfonyl¬ethanesulfonyl)-but-2-yl)        carbamic acid-(4-fluorophenyl) ester; (G.3.8);        F.VII-4) Compounds—compounds affecting cell membrane        permeability and fatty acids:        1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,        carbamatesacides: propamocarb, propamocarb-hydrochlorid,        (G.4.1);        F.VII-5)—fatty acid amide hydrolase inhibitors: oxathiapiprolin        (G.5.1-[4-[4-[5-( ), 2,6-difluorophenyl)-4,5-dihydro-{3        isoxazolyl]-[2-thiazolyl]--(1-piperidinyl]-2-[5-methyl-{[3-(trifluoromethyl)-,5-bis(di¬fluoromethyl-1H-pyrazol-1-yl]ethanone;acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2        oxazol-5-yl}phenyl methanesulfonate (G.5.2),        2-{3-[2-(1-{[3,5-bis(difluoro¬me¬thyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)        1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5 yl}-3-chlorophenyl        methanesulfonate (G.5.3);        F.VIII) H) Inhibitors with Multi Site Action        F.VIII-1) Inorganic—inorganic active substances: Bordeaux        mixture, (H.1.1), copper acetate, (H.1.2), copper hydroxide,        (H.1.3), copper oxychloride, (H.1.4), basic copper sulfate,        (H.1.5), sulfur; (H.1.6);        F.VIII-2) Thio—thio- and dithiocarbamates: ferbam, (H.2.1),        mancozeb, (H.2.2), maneb, (H.2.3), metam, methasulphocarb,        (H.2.4), metiram, (H.2.5), propineb, (H.2.6), thiram, (H.2.7),        zineb, (H.2.8), ziram; (H.2.9);        F.VIII-3) Organochlorine—organochlorine compounds (e. g.        phthalimides, sulfamides, chloronitriles):        anilazine, (H.3.1), chlorothalonil, (H.3.2), captafol, (H.3.3),        captan, (H.3.4), folpet, (H.3.5), dichlofluanid, (H.3.6),        dichlorophen, flusulfamide, hexachlorobenzene, (H.3.7),        hexachloro-benzene (H.3.8), pentachlorphenole (H.3.9) and its        salts, phthalide, (H.3.10), tolylfluanid, (H.3.11),        N-((4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;        (H.3.12);        F.VIII-4) Guanidines—guanidines and otherothers: guanidine,        (H.4.1), dodine, (H.4.2), dodine free base, (H.4.3), guazatine,        (H.4.4), guazatine-acetate, (H.4.5), iminoctadine, (H.4.6),        iminoctadine-triacetate, (H.4.7), iminoctadine-tris(albesilate)        (H.4.8), dithianon (H.4.9),        2,6-dimethyldi¬methyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone;        (H.4.10);        F.VIII-5) Ahtraquinones: dithianon;        F.IX) I) Cell wall synthesis inhibitors        F.IX-1) Inhibitors-inhibitors of glucan synthesis: validamycin,        (I.1.1), polyoxin B; (I.1.2);        F.IX-2) Melanin—melanin synthesis inhibitors: pyroquilon,        (I.2.1), tricyclazole, carpropamide, (I.2.2), carpropamid        (I.2.3), dicyclomet, (I.2.4), fenoxanil; (I.2.5);        F.X) J) Plant defence inducers        F.X-1) Salicylic acid pathway:—acibenzolar-S-methyl;        F.X-2) Others: (J.1.1), probenazole, (J.1.2), isotianil,        (J.1.3), tiadinil, (J.1.4), prohexadione-calcium;        (J.1.5); phosphonates: fosetyl, (J.1.6), fosetyl-aluminum,        (J.1.7), phosphorous acid and its salts; (J.1.8), potassium or        sodium bicarbonate (J.1.9);        F.XI) K) Unknown mode of action:    -   bronopol, (K.1.1), chinomethionat, (K.1.2), cyflufenamid,        (K.1.3), cymoxanil, (K.1.4), daz-omet, (K.1.5), debacarb,        diclomezine, (K.1.6), diclo¬mezine (K.1.7), difenzoquat,        (K.1.8), difen-zoquat-methylsulfate, (K.1.9), diphenylamin,        (K.1.10), fenpyrazamine, (K.1.11), flumetover, (K.1.12),        flusulfamide, (K.1.13), flutianil, (K.1.14), methasulfocarb,        (K.1.15), nitrapyrin, (K.1.16), nitrothal-isopropyl, (K.1.18),        oxathiapiprolin, (K.1.19), tolprocarb (K.1.20), oxin-copper,        (K.1.21), proquinazid, (K.1.22), tebufloquin, (K.1.23),        tecloftalam, (K.1.24), triazoxide, (K.1.25),        2-butoxy-6-iodo-3-propylchromen-4-one, (K.1.26),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]etha-none        (K.1.27),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl-oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thihazol-2-yl)piperidin-1-yl]ethanone        (K.1.28), 2        [3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-ylhoxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2        yl)piperidin-1-yl]ethanone (K.1.29),        N-(cyclopropylmethoxyiminocyclo¬propylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro        di¬fluoro-phenyl)-methyl)-2-phenyl acetamide, (K.1.30),        N′-(4-(4-chloro-3-trifluoromethyl-phenoxytrifluoro-methyl-phenroxy)-2,5-dimethyl-phenyl)-N-ethyl-N        methyl formamidine, (K.1.31), N′        ((4-(4-fluoro-3-trifluoromethyltrifluoro¬methyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine, (K.1.32),        N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxytrimethyl-silanyl-prop¬oxy)-phenyl)-N-ethyl-N-methyl        formamidine,forma¬midine (K.1.33), N′-(5-difluoromethyl-2        methyl-4-(3-trimethylsilanyltri¬methylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine,        2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic        acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,        2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic        acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide,        (K.1.34), methoxy-acetic acid        6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and        N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,        3-[(K.1.35), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3        yl]-pyridine (K.1.36), 3        [5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,        (pyrisoxazole,        5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1        carbothioic acid S-allyl ester, N-(6-methoxy) (K.1.37),        N-(6-meth¬oxy-pyridin-3-yl)        cyclopropanecarboxyliccyclopropane¬carboxylic acid amide,        (K.1.38), 5-chloro-1        ((4,6-dimethoxydi¬methoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,ben-zoimidazole        (K.1.39),        2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxydimeth¬oxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide,        ethyl (Z) 3 amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40),        picarbutrazox (K.1.41), pentyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxy-methyl]-2-pyridyl]carbamate        (K.1.42),        2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol        (K.1.43),        2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]¬phen-yl]propan-2-ol        (K.1.44),        3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroiso¬quinolin-1-yl)¬quinoline        (K.1.45),        3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)¬quin¬oline        (K.1.46),        3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H        1,4-benzoxazepine (K.1.48).        F.XII) Growth regulators: abscisic acid, amidochlor, ancymidol,        6-benzylaminopurine, brassino-lide, butralin, chlormequat        (chlormequat chloride), choline chloride, cyclanilide,        daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine,        ethephon, flumetralin, flurprimidol, fluthiacet,        forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic        acid, maleic hydrazide, mefluidide, mepiquat (mepiquat        chloride), naphthaleneacetic acid, N 6-benzyladenine,        paclobutrazol, pro-hexadione (prohexadione-calcium),        prohydrojasmon, thidiazuron, triapenthenol, tributyl        phos-phorotrithioate, 2,3,5 tri iodobenzoic acid,        trinexapac-ethyl and uniconazole. The commercially available        compounds of the group F listed above may be found in The        Pes-ticide Manual, 15th Edition, C. D. S. Tomlin, British Crop        Protection Council (2011) among other publications. Their        fungicides described by common names, their preparation and        their activity e.g. against harmful fungi is known (cf.:        http://www.alanwood.net/pesticides/); these substances are        commercially available. The compounds fungicides described by        IUPAC nomenclature, their preparation and their fun-gicidal        pesticidal activity are is also known (cf. Can. J. Plant Sci.        48(6), 587-94, 1968; EP A 141 317; EP-A 152 031; EP-A 226 917;        EP A 243 970; EP A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1        028 125; EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP        2002316902; DE 19650197; DE 10021412; DE 102005009458; U.S. Pat.        Nos. 3,296,272; 3,325,503; WO 98/46608; WO 99/14187; WO        99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO        01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO        03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO        03/66609; WO 03/74491; WO 04/49804; WO 04/83193; WO 05/120234;        WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO        05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO        07/90624, WO 11/028657, WO2012/168188, WO 2007/006670, WO        2011/77514; WO13/047749, WO 10/069882, WO 13/047441, WO        03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704,        WO 13/024009, WO 13/024010 and WO 13/047441, WO 13/162072, WO        13/092224, WO 11/135833).

The compounds of the invention may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same

The invertebrate pest (also referred to as “animal pest”), i.e. theinsects, arachnids and nematodes, the plant, soil or water in which theplant is growing or may grow can be contacted with the compounds of thepresent invention or composition(s) comprising them by any applicationmethod known in the art. As such, “contacting” includes both directcontact (applying the compounds/compositions directly on theinvertebrate pest or plant—typically to the foliage, stem or roots ofthe plant) and indirect contact (applying the compounds/compositions tothe locus of the invertebrate pest or plant).

The compounds of the present invention or the pesticidal compositionscomprising them may be used to protect growing plants and crops fromattack or infestation by animal pests, especially insects, acaridae orarachnids by contacting the plant/crop with a pesticidally effectiveamount of compounds of the present invention. The term “crop” refersboth to growing and harvested crops.

The compounds of the present invention and the compositions comprisingthem are particularly important in the control of a multitude of insectson various cultivated plants, such as cereal, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in formof compositions by treating the insects or the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms to beprotected from insecticidal attack with an insecticidally effectiveamount of the active compounds. The application can be carried out bothbefore and after the infection of the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms by theinsects.

Moreover, invertebrate pests may be controlled by contacting the targetpest, its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of the present invention. Assuch, the application may be carried out before or after the infectionof the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protectgrowing plants from attack or infestation by pests by contacting theplant with a pesticidally effective amount of compounds of the presentinvention. As such, “contacting” includes both direct contact (applyingthe compounds/compositions directly on the pest and/or plant—typicallyto the foliage, stem or roots of the plant) and indirect contact(applying the compounds/compositions to the locus of the pest and/orplant). “Locus” means a habitat, breeding ground, plant, seed, soil,area, material or environment in which a pest or parasite is growing ormay grow.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 5 g to 500 g per hectare, more desirably from 5g to 200 g per hectare.

The compounds of the present invention are effective through bothcontact (via soil, glass, wall, bed net, carpet, plant parts or animalparts), and ingestion (bait, or plant part).

The compounds of the present invention may also be applied againstnon-crop insect pests, such as ants, termites, wasps, flies, mosquitos,crickets, or cockroaches. For use against said non-crop pests, compoundsof the present invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics. The bait employed in thecomposition is a product, which is sufficiently attractive to inciteinsects such as ants, termites, wasps, flies, mosquitos, crickets etc.or cockroaches to eat it. The attractiveness can be manipulated by usingfeeding stimulants or sex pheromones. Food stimulants are chosen, forexample, but not exclusively, from animal and/or plant proteins (meat-,fish- or blood meal, insect parts, egg yolk), from fats and oils ofanimal and/or plant origin, or mono-, oligo- or polyorganosaccharides,especially from sucrose, lactose, fructose, dextrose, glucose, starch,pectin or even molasses or honey. Fresh or decaying parts of fruits,crops, plants, animals, insects or specific parts thereof can also serveas a feeding stimulant. Sex pheromones are known to be more insectspecific. Specific pheromones are described in the literature and areknown to those skilled in the art. For use in bait compositions, thetypical content of active ingredient is from 0.001 weight % to 15 weight%, desirably from 0.001 weight % to 5% weight % of active ingredient.

Formulations of compounds of the present invention as aerosols (e.g inspray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents such as lower alcohols (e.g. methanol,ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethylketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethylformamide, N-methylpyrrolidone,dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, amphoteric surfactants,lower epoxides, triethyl orthoformate and, if required, propellants suchas propane, butane, nitrogen, compressed air, dimethyl ether, carbondioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.Suitable repellents for example are N,N-Diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets.

The compounds of the present invention and their compositions can beused for protecting wooden materials such as trees, board fences,sleepers, etc. and buildings such as houses, outhouses, factories, butalso construction materials, furniture, leathers, fibers, vinylarticles, electric wires and cables etc. from ants and/or termites, andfor controlling ants and termites from doing harm to crops or humanbeing (e.g. when the pests invade into houses and public facilities).The compounds of the present invention are applied not only to thesurrounding soil surface or into the under-floor soil in order toprotect wooden materials but it can also be applied to lumbered articlessuch as surfaces of the under-floor concrete, alcove posts, beams,plywoods, furniture, etc., wooden articles such as particle boards, halfboards, etc. and vinyl articles such as coated electric wires, vinylsheets, heat insulating material such as styrene foams, etc. In case ofapplication against ants doing harm to crops or human beings, the antcontroller of the present invention is applied to the crops or thesurrounding soil, or is directly applied to the nest of ants or thelike.

The compounds of the present invention are also suitable for thetreatment of plant propagation material, especially seeds, in order toprotect them from insect pest, in particular from soil-living insectpests and the resulting plant's roots and shoots against soil pests andfoliar insects.

The compounds of the present invention are particularly useful for theprotection of the seed from soil pests and the resulting plant's rootsand shoots against soil pests and foliar insects. The protection of theresulting plant's roots and shoots is preferred. More preferred is theprotection of resulting plant's shoots from piercing and suckinginsects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedlings' roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the presentinvention, including a salt thereof. Particularly preferred is a method,wherein the plant's roots and shoots are protected, more preferably amethod, wherein the plants shoots are protected form piercing andsucking insects, most preferably a method, wherein the plants shoots areprotected from aphids.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing theactive compound.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens. In addition, the active compound may also be usedfor the treatment seeds from plants, which tolerate the action ofherbicides or fungicides or insecticides owing to breeding, includinggenetic engineering methods.

For example, the active compound can be employed in treatment of seedsfrom plants, which are resistant to herbicides from the group consistingof the sulfonylureas, imidazolinones, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A 142 924,EP-A 193 259), Furthermore, the active compound can be used also for thetreatment of seeds from plants, which have modified characteristics incomparison with existing plants consist, which can be generated forexample by traditional breeding methods and/or the generation ofmutants, or by recombinant procedures). For example, a number of caseshave been described of recombinant modifications of crop plants for thepurpose of modifying the starch synthesized in the plants (e.g. WO92/11376, WO 92/14827, WO 91/19806) or of transgenic crop plants havinga modified fatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment.Typcially, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight.

Seed Treatment formulations may additionally also comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a gelling agent is carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds of thepresent invention are generally from 0.01 g to 10 kg per 100 kg of seed,preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 gper 100 kg of seed.

The invention therefore also relates to seed comprising a compound ofthe present invention, including an agriculturally useful salt of it, asdefined herein. The amount of the compound of the present invention,including an agriculturally useful salt thereof will in general varyfrom 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kgper 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg ofseed. For specific crops such as lettuce the rate can be higher.

Methods which can be employed for treating the seed are, in principle,all suitable seed treatment and especially seed dressing techniquesknown in the art, such as seed coating (e.g. seed pelleting), seeddusting and seed imbibition (e.g. seed soaking). Here, “seed treatment”refers to all methods that bring seeds and the compounds of the presentinvention into contact with each other, and “seed dressing” to methodsof seed treatment which provide the seeds with an amount of thecompounds of the present invention, i.e. which generate a seedcomprising a compound of the present invention. In principle, thetreatment can be applied to the seed at any time from the harvest of theseed to the sowing of the seed. The seed can be treated immediatelybefore, or during, the planting of the seed, for example using the“planter's box” method. However, the treatment may also be carried outseveral weeks or months, for example up to 12 months, before plantingthe seed, for example in the form of a seed dressing treatment, withouta substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein,the term “unsown seed” is meant to include seed at any period from theharvest of the seed to the sowing of the seed in the ground for thepurpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seedis mixed, in a suitable device, for example a mixing device for solid orsolid/liquid mixing partners, with the desired amount of seed treatmentformulations, either as such or after previous dilution with water,until the composition is distributed uniformly on the seed. Ifappropriate, this is followed by a drying step.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, are in particular alsosuitable for being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions comprising a parasiticidallyeffective amount of compounds of the present invention, including theirstereoisomers, veterinarily acceptable salts or N-oxides, and anacceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention, including itsstereoisomers, veterinarily acceptable salts or N-oxides, or acomposition comprising it.

The invention also provides the use of a compound of the presentinvention, including its stereoisomers, veterinarily acceptable salts orN-oxides, for treating or protecting an animal from infestation orinfection by invertebrate pests.

The invention also provides a process for the preparation of acomposition for treating, controlling, preventing or protecting animalsagainst infestation or infection by parasites which comprises aparasiticidally effective amount of a compound of the present invention,including its stereoisomers, veterinarily acceptable salts or N-oxides,or a composition comprising it.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula (I) andtheir stereoisomers, veterinarily acceptable salts, tautomers andN-oxides, are suitable for combating endo- and ectoparasites in and onanimals.

The compounds of the present invention, especially compounds of formula(I) and their stereoisomers, veterinarily acceptable salts, tautomersand N-oxides, and compositions comprising them are preferably used forcontrolling and preventing infestations of and infections in animalsincluding warm-blooded animals (including humans) and fish. They are forexample suitable for controlling and preventing infestations andinfections in mammals such as cattle, sheep, swine, camels, deer,horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo,donkeys, fallow deer and reindeer, and also in fur-bearing animals suchas mink, chinchilla and raccoon, birds such as hens, geese, turkeys andducks and fish such as fresh- and salt-water fish such as trout, carpand eels.

Compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are preferably used for controlling and preventing infestations andinfections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are suitable for systemic and/or non-systemic control of ecto-and/or endoparasites. They are active against all or some stages ofdevelopment.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus,

cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattellaasahinae, Periplaneta americana, Periplaneta japonica, Periplanetabrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blattaorientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedesvexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anophelesleucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphoravicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria,Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyiahominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens,Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culisetainornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis,Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis,Glossina fuscipes, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconopstorrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrusovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simuliumvittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanuslineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp.,

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Ariluscritatus, Anoplurida, e.g. Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp., and Solenopotes spp.,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp.,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.,

Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobusspp.,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchuscontortus., Ostertagia spp., Cooperia spp., Nematodirus spp.,Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurusdentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamustrachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necatorspp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi, Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp.,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp.,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeuticuse of compounds of the present invention and compositions comprisingthem for controlling and/or combating parasites in and/or on animals.The compounds of the present invention and compositions comprising themmay be used to protect the animals from attack or infestation byparasites by contacting them with a parasiticidally effective amount ofcompounds of the present invention and compositions containing them. Thecompounds of the present invention and compositions comprising them canbe effective through both contact (via soil, glass, wall, bed net,carpet, blankets or animal parts) and ingestion (e.g. baits). As such,“contacting” includes both direct contact (applying the pesticidalmixtures/compositions containing the compounds of the present inventiondirectly on the parasite, which may include an indirect contact at itslocus-P, and optionally also administrating the pesticidalmixtures/composition directly on the animal to be protected) andindirect contact (applying the compounds/compositions to the locus ofthe parasite). The contact of the parasite through application to itslocus is an example of a non-therapeutic use of compounds of the presentinvention. “Locus-P” as used above means the habitat, food supply,breeding ground, area, material or environment in which a parasite isgrowing or may grow outside of the animal.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions of the presentinvention. A parasiticidally effective amount of the compositions willalso vary according to the prevailing conditions such as desiredparasiticidal effect and duration, target species, mode of application,and the like.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically andtherapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

The compounds of the invention are better bio-degradable than those ofthe prior art and in addition retain a high level of pest control. Thismakes them superior in terms of environmental safety. In light of thestructural similarities of the compounds of formula I, this significantdifference in bio-degradability in favour of the compounds of theinvention is unexpected and cannot be derived from what is known fromthe prior art.

EXAMPLES

The present invention is now illustrated in further details by thefollowing examples, without imposing any limitation thereto.

ABBREVIATIONS

-   TLC thin layer chromatography-   r.t. room temperature (20-25° C.)-   PE petrol ether-   TFA trifluoroacetic acid-   EtOAc ethyl acetate-   THF tetrahydrofuran-   t-BuOH tert-butanol-   DMAP 4-(dimethylamino)-pyridine-   LDA lithiumdiisopropylamide-   TsCl tosylchloride-   MTBE methyl-tert-butyl ether-   DMF N,N-dimethylformamide-   DCM dichloromethane-   PyBrOP bromo-tris-pyrrolidino phosphoniumhexafluorophosphate-   NBS N-bromosuccinimide-   MeOH methanol-   TEA trimethylamine-   dppf 1,1′-bis(diphenylphosphino)ferrocen-   MeCN acetonitrile-   EtOH ethanol-   m-CPBA meta-chloroperbenzoic acid-   PPh₃ triphenylphosphine

I. Preparation Examples

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by theirmelting points.

Analytical HPLC column:

HPLC method 1: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm; mobilephase: A: water+0.1% trifluoroacetic acid (TFA); B: acetonitrile+0.1%TFA; gradient: 5-100% B in 1.50 minutes; 100% B 0.20 min; flow: 0.8-1.0ml/min in 1.51 minutes at 60° C.

HPLC method 2: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm; mobilephase: A: water+0.1% trifluoroacetic acid (TFA); B: acetonitrile+0.1%TFA; gradient: 5-100% B in 1.25 minutes; 100% B 0.70 min; flow: 0.8-1.0ml/min in 1.51 minutes at 60° C. MS method: ESI positive, Mass range(m/z): 100-700.

¹H-NMR: The signals are characterized by chemical shift (ppm) vs.tetramethylsilane, by their multiplicity and by their integral (relativenumber of hydrogen atoms given). The following abbreviations are used tocharacterize the multiplicity of the signals: m=multiplett, q=quartett,t=triplett, d=doublet and s=singlett.

Preparation Examples Example 1: Synthesis of4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1,1-dioxothietan-3-yl)-2,3-dihydrobenzothiophene-7-carboxamide(Compound I-7) Step 1: Preparation of tert-butyl4-bromo-2-fluoro-benzoate

To a solution of 4-bromo-2-fluoro-benzoic acid (100.0 g, 0.46 mol) inTHF/t-BuOH (800 mL/400 mL) was added Boc₂O (150.0 g, 0.69 mol) and DMAP(5.6 g, 46.0 mmol), the mixture was stirred at 80° C. for 13 h. TLC(PE:EtOAc=10:1) showed the reaction was completed. After removal of thesolvent, the residue was dissolved in water and extracted with EtOAc(500 mL×3), the organic layer was dried over Na₂SO₄ and concentrated togive the crude product, which was purified by column chromatography(PE:EtOAc=100:1) to give the title compound (120.0 g, 95.5%) as acolorless oil.

¹H-NMR (400 MHz, CDCl₃): δ=7.69-7.78 (m, 1H) 7.26-7.34 (m, 2H) 1.58 (s,9H)

Step 2: tert-Butyl 4-bromo-2-fluoro-3-(2-hydroxyethyl)benzoate

To a solution of tert-butyl 4-bromo-2-fluoro-benzoate (60.0 g, 0.22 mol)in THF was added LDA (130 mL, 0.26 mol) drop wise at −78° C., themixture was stirred at this temperature for 4 h, then oxirane (77.0 g,1.75 mol) was added. The mixture was stirred at this temperature foranother 6 h, then the reaction mixture was poured into aq. NH₄Cl (300mL) and extracted with EtOAc (400 mL×3). The organic layer was driedover Na₂SO₄ and concentrated to give the crude product, which waspurified by silica gel chromatograph (PE:EtOAc=10:1˜5:1) to give thetitle compound (14.0 g, 20.0%) as a yellow solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.61 (t, J=8.03 Hz, 1H) 7.40 (d, J=8.28 Hz,1H) 3.87 (t, J=6.90 Hz, 2H) 3.16 (t, J=6.90, 2.51 Hz, 2H) 1.60 (s, 9H)

Step 3: tert-Butyl4-bromo-2-fluoro-3-[2-(p-tolylsulfonyloxy)ethyl]benzoate

To a solution of tert-butyl 4-bromo-2-fluoro-3-(2-hydroxyethyl)benzoate(10.0 g, 31.4 mmol) in pyridine was added TsCl (9.0 g, 47.2 mmol) inportions at 0° C. The mixture was stirred at 15° C. for 14h. TLC(PE:EtOAc=10:1) showed the reaction was complete. After removal of thesolvent, the residue was dissolved in water, extracted with MTBE (200mL×3), the organic layer was dried over Na₂SO₄ and concentrated to givethe crude product (17 g), which was used directly in the next stepwithout further purification.

¹H-NMR (400 MHz, CDCl₃): δ=7.61 (t, J=8.16 Hz, 1H) 7.40 (d, J=8.82 Hz,1H) 3.87 (t, =6.84 Hz, 2H) 3.15 (td, =6.84, 2.65 Hz, 2H) 1.59 (s, 9H)

Step 4: tert-Butyl 4-bromo-2,3-dihydrobenzothiophene-7-carboxylate

To a solution of tert-butyl4-bromo-2-fluoro-3-[2-(p-tolylsulfonyloxy)ethyl]benzoate (17.0 g crude,54.1 mmol) in DMF (200 mL) was added Na₂S (5.0 g, 65.0 mmol), themixture was stirred at 60° C. for 14 h. TLC (PE:EtOAc=10:1) showed thereaction was complete. After removal of the solvent, the residue wasdissolved in EtOAc and washed with water (100 mL×2), the organic layerwas dried over Na₂SO₄ and concentrated to give the crude product, whichwas purified by column chromatography (PE:EtOAc=10:1) to give the titlecompound (6.9 g, 70.0% for 2 steps) as a colorless oil.

¹H-NMR (400 MHz, CDCl₃): δ=7.62 (d, J=8.38 Hz, 1H) 7.19 (d, J=8.38 Hz,1H) 3.38 (d, J=7.06 Hz, 2H) 3.31 (d, J=7.06 Hz, 2H) 1.60 (s, 9H)

Step 5: tert-butyl 4-acetyl-2,3-dihydrobenzothiophene-7-carboxylate

To a solution of tert-butyl4-bromo-2,3-dihydrobenzothiophene-7-carboxylate (6.9 g, 22.0 mmol) inDMF/H₂O (200 mL/60 mL) was added K₂CO₃ (6.2 g, 44.9 mmol) andPd(PPh₃)2Cl₂ (0.34 g, 0.44 mmol), then tributyl(1-ethoxyvinyl)stannane(9.5 g, 26.4 mmol) was added, the mixture was stirred at 110° C. underN₂ for 3 h. TLC (PE:EtOAc=5:1) showed the reaction was completed. To theresulting mixture was added KF (50 g) and stirred for an additional 1 h.After removal of the solvent, the residue was dissolved in water andextracted with EtOAc (100 mL×3), the organic layer was dried over Na₂SO₄and concentrated, then the residue was dissolved in aq. HCl/THF (0.6 M)and stirred for 12 h. After that, it was extracted with EtOAc (100mL×3), the organic layer was dried over Na₂SO₄ and concentrated to givethe crude product, which was purified by column chromatography(PE:EtOAc=20:1) to give the title compound (2.8 g, 45.8%) as a yellowsolid.

¹H-NMR (400 MHz, CDCl₃): δ=7.86 (d, J=7.94 Hz, 1H) 7.48 (d, J=7.94 Hz,1H) 3.62 (t, J=8.16 Hz, 2H), 3.21-3.31 (m, 2H) 2.60 (s, 3H) 1.62 (s, 9H)

Step 6: tert-Butyl4-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2,3-dihydrobenzothiophene-7-carboxylate

To a solution of tert-butyl4-acetyl-2,3-dihydrobenzothiophene-7-carboxylate (2.8 g, 10.1 mmol) and1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone 3 (5.2 g, 20.1mol) in 1,2-dichloroethane (80 mL) was added K₂CO₃ (2.1 g, 15.1 mmol),then triethylamine (1.5 g, 15.1 mmol) was added. The mixture was stirredfor at 120° C. under N₂ for 14 h. TLC (PE:EtOAc=10:1) showed thereaction was complete. After removal of the solvent, the residue waspurified by silica gel chromatography (PE:EtOAc=80:1) to give the titlecompound (6.0 g, crude as a mixture of E/Z isomers) as a yellow solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.30-7.36 (m, 2H) 7.21 (d, J=6.02 Hz, 2H)3.45-3.53 (m, 2H) 3.22-3.32 (m, 2H), 1.64 (s, 9H)

Step 7: tert-Butyl4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzothiophene-7-carboxylate

To a solution of tert-butyl4-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2,3-dihydrobenzothiophene-7-carboxylate(6.0 g crude, 11.5 mol) in 1,2-dichloroethane (120 mL) was added NH₂OHHCl (1.6 g. 23.0 mmol) and tetrabutylammoniumbromide (0.6 g, 1.9 mmol),then a solution of NaOH (1.8 g, 45.0 mmol) in water (30 mL) was addeddrop wise. The mixture was stirred for 3 h, TLC (PE:EtOAc=10:1) showedthe reaction was complete. Then the reaction solution was separated andthe organic layer was dried over Na₂SO₄, concentrated to give the crudeproduct, which was purified by silica gel chromatograph (PE:EtOAc=80:1)to give the title compound (3.8 g, 70.3% for 2 steps) as a solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.84 (d, J=7.94 Hz, 1H) 7.59 (d, J=6.17 Hz,2H) 7.01 (d, J=8.38 Hz, 1H) 4.14 (d, J=17.20 Hz, 1H) 3.75 (d, J=17.20Hz, 1H) 3.64 (q, J=8.09 Hz, 2H) 3.29-3.38 (m, 2H) 1.63 (s, 9H)

Step 8:4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzothiophene-7-carboxylicacid

To a solution of tert-butyl4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzothiophene-7-carboxylate(3.8 g, 7.1 mmol) in DCM (100 mL) was added TFA (30 mL), then themixture was stirred at r.t. for 3 h. TLC (PE:EtOAc=10:1) showed thereaction was complete. After removal of the solvent, the residue waswashed with hexane to give the title compound (2.8 g, 82%) as a solid.

¹H-NMR (400 MHz, DMSO-d₆): δ=13.29 (br. s., 1H) 7.75-7.91 (m, 4H) 7.35(d, J=7.94 Hz, 1H) 4.30-4.43 (m, 2H), 3.45-3.52 (m, 2H) 3.21-3.28 (m,2H)

Step 9:4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1,1-dioxothietan-3-yl)-2,3-dihydrobenzothiophene-7-carboxamide(compound I-7)

To a solution of4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzothiophene-7-carboxylicacid (200 mg, 0.42 mmol), 1,1-dioxothietan-3-amine hydrochloride (0.08g, 0.5 mmol, 1.2 equiv.) and PyBrop (0.23 g, 0.5 mmol, 1.2 equiv.) indichloromethane (20 mL) was added Hünig base (0.17 g, 1.33 mmol, 3.2equiv.) at room temperature. The mixture was stirred over night and asaturated aqueous solution of NH₄Cl was added. Extraction withdichloromethane (50 mL×2) afforded an organic layer that was washed withwater, dried over Na₂SO₄ and concentrated in vacuum. Purification of theresidue via silica gel chromatography afforded the title compound (190mg, 76%).

¹H-NMR (400 MHz, CDCl₃): δ=7.59 (m, 3H), 7.28 (m, 1H), 7.01 (m, 1H),4.86 (m, 1H), 4.61 (m, 2H), 4.15 (m, 3H), 3.76 (d, 1H), 3.50-3.68 (m,2H), 3.31 (m, 2H).

Example 2

In analogy to steps 5 to 9 of example 1, compounds of the formulae I-1to I-5, I-11 to I-12, I-14 to I-19 and I-28 were prepared. The startingmaterial tert-butyl 4-bromo-2,3-dihydrobenzofuran-7-carboxylate was usedinstead.

Step 1: tert-Butyl 4-bromo-2,3-dihydrobenzofuran-7-carboxylate

To a solution of tert-butyl 4-bromo-2-fluoro-3-(2-hydroxyethyl)benzoate(10.0 g, 31.4 mmol) in DMF (2 L) was added Cs₂C₀₃ (15.4 g, 47.2 mmol),the mixture was stirred at 90° C. for 14 h. TLC (PE:EtOAc=5:1) showedthe reaction was complete. After removal of the solvent, the residue wasdissolved in water and extracted with EtOAc (300 mL×3), the organiclayer was dried over Na₂SO₄ and concentrated to give the crude product,which was purified by column chromatography (PE:EtOAc=10:1) to give thetitle compound (6.5 g, 69.5%) as a solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.52 (d, J=8.38 Hz, 1H) 6.98 (d, J=8.82 Hz,1H) 4.75 (t, J=8.82 Hz, 2H) 3.21 (t, J=8.82 Hz, 2H) 1.57 (s, 9H).

Example 3

In analogy to steps 5 to 9 of example 1, compounds of the formulae I-22to I-24, I-29, I-35 to I-41 were prepared. The starting material methyl7-bromo-1,3-dihydroisobenzofuran-4-carboxylate was used instead.

Step 1: 1,2-Bis(bromomethyl)-3-nitro-benzene

To a solution of 1,2-dimethyl-3-nitro-benzene (102 g, 0.675 mol) and NBS(258.3 g, 1.45 mol) in CCl₄ (450 mL) was added benzoyl peroxide (1.68 g,6.8 mmol) in one portion. The reaction mixture was stirred and refluxedat 90° C. under N₂ for 2 h, additional benzoyl peroxide (6.5 g, 0.027mol) was added and the reaction mixture was stirred and refluxed at 90°C. under N₂ for 2 h and then cooled to room temperature. The reactionmixture was filtered and washed with CCl₄. The yellow filtrate wasconcentrated to give 1,2-bis(bromomethyl)-3-nitrobenzene as a crude oil.The crude product was purified by column chromatography (PE:EtOAc=60:1)to give the title compound (crude 180 g, 87.3%) as an oil.

¹H-NMR (400 MHz, CDCl₃): δ=7.85 (d, J=7.94 Hz, 1H) 7.73 (d, J=7.94 Hz,1H) 7.47-7.55 (m, 1H) 4.87 (s, 2H) 4.78 (s, 2H).

Step 2: 4-Nitro-1,3-dihydroisobenzofuran

To a flask containing 1,2-bis(bromomethyl)-3-nitro-benzene (180 g, 0.59mol,) was added neutralized alumina (816 g, 8 mol) and toluene (1 L) andthe suspension was heated at an external temperature of 120° C. for 18hours. The reaction mixture was filtered to remove the alumina andwashed with ethyl acetate. The filtrate was concentrated to give ayellow solid which was purified by silica gel chromatography(PE:EtOAc=20:1) to give the title compound (17.5 g, 18%) as an oil.

¹H-NMR (400 MHz, CDCl₃): δ=8.14 (d, J=7.94 Hz, 1H), 7.55-7.59 (m, 1H),7.47-7.52 (m, 1H), 5.54 (s, 2H), 5.21 (s, 2H).

Step 3: 1,3-Dihydroisobenzofuran-4-amine

A solution of 4-nitro-1,3-dihydroisobenzofuran (50 g, 0.303 mol) in MeOH(800 mL) was hydrogenated with Pd/C (5 g) under H₂ at 50 psi. Thereaction was filtered and then concentrated to give the desired titlecompound (35 g, 85.5%) as a solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.05-7.15 (m, 1H), 6.68 (d, J=7.15 Hz, 1H),6.58 (d, J=7.65 Hz, 1H), 5.12 (br. s., 2H), 5.04 (br. s., 2H), 3.56 (br.s., 2H).

Step 4: tert-Butyl N-(1,3-dihydroisobenzofuran-4-yl)carbamate

To a solution of 1,3-dihydroisobenzofuran-4-amine (36 g, 0.267 mol) inTHF (500 mL) was added TEA (54.4 g, 0.533 mol) and Boc₂O (87.2 g, 0.400mol) in dropwise. The mixture was stirred and heated at an externaltemperature of 80° C. for 6 h. The reaction was filtered, diluted intowater (300 mL), extracted with EtOAc (500 mL×3), the organic layer waswashed brine (100 mL), dried over Na₂SO₄, filtered and concentratedunder reduce pressure to give the crude product. The crude product waspurified by column chromatography (PE:EtOAc=30:1) to give the titlecompound (35 g, 55.9%) as a solid.

¹H-NMR (400 MHz, CDCl₃): δ=7.59 (d, J=7.94 Hz, 1H), 7.23-7.32 (m, 1H),6.98 (d, J=7.50 Hz, 1H), 6.30 (br. s., 1H), 5.15 (s, 2H), 5.11 (s, 2H),1.55 (s, 9H).

Step 5: tert-Butyl N-(7-bromo-1,3-dihydroisobenzofuran-4-yl)carbamate

To a solution of tert-butyl N-(1,3-dihydroisobenzofuran-4-yl)carbamate(25 g, 0.085 mol) in DMF (300 mL), NBS (16.6 g, 0.094 mol) was added inportions at 0° C. The reaction mixture was stirred at 25° C. under N₂for 3 h. The reaction was filtered, diluted into water (1000 mL),extracted with EtOAc (500 mL×3), the organic layer was washed brine (300mL), dried over Na₂SO₄, filtered and concentrated under reduced pressureto give the crude product. The crude product was purified by columnchromatography (PE:EtOAc=50:1) to give the title compound (25 g, 74.8%).

¹H-NMR (400 MHz, CDCl₃): δ=7.49 (d, J=8.28 Hz, 1H), 7.33 (d, J=8.53 Hz,1H), 6.26 (br. s., 1H), 5.16 (s, 2H), 5.08 (s, 2H), 1.51 (s, 9H).

Step 6: Methyl7-(tert-butoxycarbonylamino)-1,3-dihydroisobenzofuran-4-carboxylate

To a stirred solution of tert-butylN-(7-bromo-1,3-dihydroisobenzofuran-4-yl)carbamate (30 g, 0.095 mol) inMeOH (800 mL) in a 1 L autoclave, Na₂CO₃ (30.4 g, 0.286 mol) andPd(dppf)Cl₂ (5 g) was added, the mixture was stirred and heated at 120°C. under CO at 1 MPa for 18 h. After cooling to room temperature, themixture was filtered, concentrated, the residue was purified bychromatography on silica gel (PE:EtOAc=10:1) to give the title compound(24 g, 85.7%).

¹H-NMR (400 MHz, CDCl₃): δ=7.93 (q, J=8.53 Hz, 2H) 6.28 (br. s., 1H)5.42 (s, 2H) 5.10 (s, 2H) 3.90 (s, 3H) 1.55 (s, 9H).

Step 7: Methyl 7-amino-1,3-dihydroisobenzofuran-4-carboxylate

To a stirred solution of methyl7-(tert-butoxycarbonylamino)-1,3-dihydroisobenzofuran-4-carboxylate (20g, 0.095 mol) in DCM (800 mL), TFA (80 mL) was added dropwise at OoC,the mixture was stirred at 18° C. for 18 h. The mixture wasconcentrated, diluted into aq. Na₂CO₃ solution (500 mL), extracted withEtOAc (300 mL×3) dried over Na₂SO₄, concentrated to give the titlecompound (15 g, crude).

¹H-NMR (400 MHz, CDCl₃): δ=7.76 (d, J=8.28 Hz, 1H) 6.56 (d, J=8.28 Hz,1H) 5.35 (s, 2H) 4.99 (s, 2H) 3.83 (s, 3H)

Step 8: Methyl 7-bromo-1,3-dihydroisobenzofuran-4-carboxylate

To a stirred solution of methyl7-amino-1,3-dihydroisobenzofuran-4-carboxylate (15 g, 0.078 mol) in MeCN(500 mL), CuBr (16.8 g, 0.116 mol) and tert-butyl nitrite (12 g, 0.116mol) was added, the mixture was stirred at 68° C. for 18 h. The mixturewas filtered, concentrated, the residue was purified by chromatographyon silica gel (PE:EtOAc=50:1) to give the title compound (15 g, crude).

¹H-NMR (400 MHz, CDCl₃): δ=8.05 (d, J=7.94 Hz, 1H) 7.86 (d, J=7.94 Hz,1H) 5.38 (dd, J=10.36, 1.54 Hz, 4H) 3.95 (s, 3H) 2.64 (s, 3H).

Example 4

In analogy to example 3, compounds of formulae I-51 and I-52 wereprepared using 4-nitro-1,3-dihydro-2-benzothiophene as starting material

To a solution of 1,2-bis(bromomethyl)-3-nitro-benzene (185.0 g, 0.6 mol)in EtOH (3 L) was added the Na₂S.9H2O (144.2 g, 0.6 mol), then themixture was heated under reflux for 10 h. The mixture was concentratedto remove EtOH, then water (500 mL) was added and extracted with DCM(500 mL×4), the combined organic layer was washed with brine (300 mL×2),dried over Na₂SO₄ and concentrated, purified by silica gel columnchromatography (PE:EtOAc=50: 1 to 20:1) to give the title compound (80.1g, yield 36.9%).

¹H-NMR (400 MHz, CDCl₃): δ=4.34 (s, 2H) 4.72 (s, 2H) 7.38-7.48 (m, 1H)7.57 (d, J=7.5 Hz, 1H) 8.11 (d, J=8.4 Hz, 1H).

Example 5:7-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,2-dioxo-1,3-dihydro-2-benzothiophene-4-carboxylicacid

To a solution of7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-1,3-dihydro-2-benzothiophene-4-carboxylicacid (2.5 g, 0.0052 mol) in DCM (100 mL) was added m-CPBA (2.4 g, 0.0115mol) at 0° C. Then it was stirred at 20° C. under N₂ for 12 h. Thereaction mixture was concentrated. The crude product was purified bypreparative HPLC to give the title compound (1.5 g, 58%).

¹H-NMR (400 MHz, CDCl₃): δ=4.33-4.51 (m, 2H) 4.63 (d, J=5.29 Hz, 2H)4.77 (s, 2H) 7.71-7.85 (m, 3H) 8.07 (d, J=8.38 Hz, 1H).

Example 6

In analogy to example 5, all other sulfur oxidation products, such ascompounds I-42 to I-50 were prepared.

Example 7: Synthesis ofN-[[4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methyl]butanamide(compound I-16) Step 1:[4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methanol

To a solution of4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-carboxylicacid (6 g, 13 mmol) in THF (100 mL) was added BH₃.Me₂S (3.9 mL, 39 mmol)at 0° C. The mixture was stirred at 25° C. for 15 h. The reactionmixture was quenched with MeOH (39 mL) and concentrated to give theproduct, which was purified by column chromatography(PE:EtOAc=20:1˜10:1) to give the title compound (4 g, 69%).

¹H-NMR (400 MHz, CDCl₃): δ=3.42-3.52 (m, 2H) 3.73 (d, J=17.07 Hz, 1H)4.14 (br. s., 1H) 4.64-4.73 (m, 4H) 6.82 (d, J=7.78 Hz, 1H) 7.20 (d,J=7.78 Hz, 1H) 7.59 (d, J=6.02 Hz, 2H).

Step 2:[4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methylmethanesulfonate

To a solution of[4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methanol(4 g, 9 mmol) in DCM (60 mL) was added TEA (2.7 g, 27 mmol) and MsCl (2g, 18 mmol) at 0° C. The mixture was stirred at 25° C. for 10 h. Thenthe reaction mixture was diluted with aq. NH₄Cl (100 mL) and extractedwith EtOAc (100 mL×3), the combined organic layers were dried overNa₂SO₄ and concentrated, then the residue was purified by silica gelchromatograph (PE:EtOAc=15:1˜10:1) to give the title compound (4.6 g,98%).

¹H-NMR (400 MHz, CDCl₃): δ=3.16 (s, 3H) 3.46-3.57 (m, 2H) 3.70 (s, 1H)4.16 (s, 1H) 4.61 (s, 2H) 4.72 (t, J=8.91 Hz, 2H) 6.84 (d, J=8.03 Hz,1H) 7.23-7.29 (m, 1H) 7.60 (d, J=6.02 Hz, 2H)

Step 3:3-[7-(Azidomethyl)-2,3-dihydrobenzofuran-4-yl]-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazole

To a solution of[4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methylmethanesulfonate (4.6 g, 9 mmol) in DMF (60 mL) was added NaN₃ (1.2 g,18 mmol) and the mixture was stirred at 25° C. under N₂ for 13 h. Thereaction mixture was diluted with water (100 mL) and extracted with MTBE(100 mL×3), the combined organic layers are dried over with Na₂SO₄ andconcentrated to give the title compound (4 g, 97.6%).

¹H-NMR (400 MHz, CDCl₃): δ=3.38-3.49 (m, 2H) 3.71 (d, J=17.64 Hz, 1H)4.06-4.11 (m, 1H) 4.27 (br. s., 2H) 4.60 (t, J=8.82 Hz, 2H) 6.80 (d,J=7.94 Hz, 1H) 7.08 (d, J=7.94 Hz, 1H) 7.53 (d, J=5.73 Hz, 2H).

Step 4:[4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methanamine

To a solution of3-[7-(azidomethyl)-2,3-dihydrobenzofuran-4-yl]-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazole(4 g, 8 mmol) in THF (80 mL) and H₂O (80 mL) was added PPh₃ (2.7 g, 10mmol), the mixture was stirred at 85° C. under N₂ for 2 h. The mixturewas extracted with EtOAc (100 mL×3), the combined organic layers aredried over Na₂SO₄ and concentrated, then the residue was purified bysilica gel chromatography (DCM:MeOH=15:1˜10:1) to give the titlecompound (1.5 g, 40%).

¹H-NMR (400 MHz, CDCl₃): δ=3.39-3.54 (m, 2H) 3.72 (d, J=17.20 Hz, 1H)3.83 (s, 2H) 4.12 (d, J=17.20 Hz, 1H), 4.66 (t, J=8.82 Hz, 2H) 6.80 (d,J=7.50 Hz, 1H) 7.13 (d, J=7.94 Hz, 1H) 7.59 (d, J=6.17 Hz, 2H).

Step 5:N-[[4-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methyl]butanamide(compound I-16)

To a solution of4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2,3-dihydrobenzofuran-7-yl]methanamine(0.15 g, 0.33 mmol) in THF (10 mL) was added triethylamine (0.07 g, 0.67mmol, 2.0 equiv.), followed by n-butyric chloride (0.04 g, 0.4 mmol, 1.2equiv.) at room temperature and stirred over night. The reaction mixturewas concentrated in vacuum and the residue was purified via silica gelchromatography to yield the title compound (0.11 g, 65%).

¹H-NMR (400 MHz, CDCl₃): δ=0.93 (t, 3H), 1.63 (m, 2H), 2.18 (m, 2H),3.37-3.55 (m, 2H), 3.72 (d, 1H), 4.11 (d, 1H), 4.40 (m, 1H), 4.65 (m,2H), 6.10 (br. s, 1H), 6.79 (m, 1H), 7.17 (m, 1H), 7.69 (m, 2H).

In analogy to the above described examples, compounds I-1 to I-57 asshown in tables C.1 and C.2 were prepared.

TABLE C.1 compounds of formula I-A with R^(2a) = R^(2c) = Cl, R^(2b) = Fm/z No. R^(g1) R^(g2) A method t_(R) [min] [M + H]⁺ I-1 #—CH₂—CH₂—O—*pyrimidin-2-ylmethylcarbamoyl 1 1.354 554.9 I-2 #—CH₂—CH₂—O—*(1,1-dioxothietan-3-yl)carbamoyl 1 1.341 567.0 I-3 #—CH₂—CH₂—O—*[2-oxo-2-(2,2,2- 1 1.366 602.1 trifluoroethylamino)ethyl]carbamoyl I-4#—CH₂—CH₂—O—* 2-pyridylmethylcarbamoyl 1 1.169 554.1 I-5 #—CH₂—CH₂—O—*[2-(allylamino)-2-oxo- 1 1.336 560.1 ethyl]carbamoyl I-6 #—CH₂—CH₂—S—*pyrimidin-2-ylmethylcarbamoyl 1 1.356 570.9 I-7 #—CH₂—CH₂—S—*(1,1-dioxothietan-3-yl)carbamoyl see Example 1 I-8 #—CH₂—CH₂—S—*[2-oxo-2-(2,2,2- 1 1.353 618.0 trifluoroethylamino)ethyl]carbamoyl I-9#—CH₂—CH₂—S—* 2-pyridylmethylcarbamoyl 1 1.192 570.0 I-10 #—CH₂—CH₂—S—*[2-(allylamino)-2-oxo- 1 1.347 576.0 ethyl]carbamoyl I-11 #—CH₂—CH₂—O—*(3,3,3- 1 1.407 559.0 trifluoropropanoylamino)methyl I-12 #—CH₂—CH₂—O—*[(4S)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.387 576.0 yl]carbamoyl I-13#—CH₂—CH₂—S—* [(4S)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.385 592.0yl]carbamoyl I-14 #—CH₂—CH₂—O—* [(2-ethylsulfonylacetyl)amino]methyl 11.334 583.0 I-15 #—CH₂—CH₂—O—* (cyclopropanecarbonylamino)methyl 1 1.385517.0 I-16 #—CH₂—CH₂—O—* (butanoylamino)methyl 1 1.402 519.0 I-17#—CH₂—CH₂—O—* acetamidomethyl 1 1.318 491.0 I-18 #—CH₂—CH₂—O—*(propanoylamino)methyl 1 1.360 505.0 I-19 #—CH₂—CH₂—O—* [(2- 1 1.306569.1 methylsulfonylacetyl)amino]methyl I-20 #—CH₂—CH₂—S(═O)—*pyrimidin-2-ylmethylcarbamoyl 1 1.146 586.9 I-21 #—CH₂—CH₂—S(═O)₂—*pyrimidin-2-ylmethylcarbamoyl 1 1.215 602.9 I-22 #—CH₂—O—CH₂—*[2-oxo-2-(2,2,2- 1 1.331 601.9 trifluoroethylamino)ethyl]carbamoyl I-23#—CH₂—O—CH₂—* (2-ethyl-3-oxo-isoxazolidin-4- 1 1.336 576.0 yl)carbamoylI-24 #—CH₂—O—CH₂—* pyrimidin-2-ylmethylcarbamoyl 1 1.303 555.0 I-26#—CH₂—CH₂—CH₂—O—* methoxycarbonyl 1 1.443 492.0 I-27 #—CH₂—CH₂—CH₂—O—*CO₂H 1 1.341 477.9 I-28 #—CH₂—CH₂—O—* (2-ethyl-3-oxo-isoxazolidin-4- 11.404 576.0 yl)carbamoyl I-29 #—CH₂—O—CH₂—* 2-pyridylmethylcarbamoyl 11.154 554.0 I-30 #—CH₂—CH₂—CH₂—O—* pyrimidin-2-ylmethylcarbamoyl 1 1.352569.0 I-31 #—CH₂—CH₂—CH₂—O—* 2-pyridylmethylcarbamoyl 2 1.162 568.0 I-32#—CH₂—CH₂—CH₂—O—* [2-oxo-2-(2,2,2- 1 1.357 616.0trifluoroethylamino)ethyl]carbamoyl I-33 #—CH₂—CH₂—CH₂—O—*(1,1-dioxothietan-3-yl)carbamoyl 1 1.328 580.9 I-34 #—CH₂—CH₂—CH₂—O—*[(4R)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.376 590.0 yl]carbamoyl I-35#—CH₂—O—CH₂—* [2-(allylamino)-2-oxo- 1 1.300 229.6 ethyl]carbamoyl I-36#—CH₂—O—CH₂—* cyclobutylcarbamoyl 1 1.423 516.7 I-37 #—CH₂—O—CH₂—*thietan-3-ylcarbamoyl 1 1.372 534.9 I-38 #—CH₂—O—CH₂—*cyclopropylmethylcarbamoyl 1 1.377 517.0 I-39 #—CH₂—O—CH₂—*cyclopropylcarbamoyl 1 1.325 502.9 I-40 #—CH₂—O—CH₂—*[(4S)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.296 575.9 yl]carbamoyl I-41#—CH₂—O—CH₂—* (1,1-dioxothietan-3-yl)carbamoyl 1 1.259 567.0 I-42#—CH₂—S(═O)₂—CH₂—* pyrimidin-2-ylmethylcarbamoyl 1 1.239 602.6 I-43#—CH₂—S(═O)₂—CH₂—* 2-pyridylmethylcarbamoyl 1 1.137 603.4 I-44#—CH₂—S(═O)₂—CH₂—* [2-oxo-2-(2,2,2- 1 1.235 649.9trifluoroethylamino)ethyl]carbamoyl I-45 #—CH₂—S(═O)₂—CH₂—*[2-(allylamino)-2-oxo- 1 1.206 608.0 ethyl]carbamoyl I-46#—CH₂—S(═O)₂—CH₂—* cyclobutylcarbamoyl 1 1.297 565.0 I-47#—CH₂—S(═O)₂—CH₂—* cyclopropylmethylcarbamoyl 1 1.332 564.6 I-48#—CH₂—S(═O)₂—CH₂—* cyclopropylcarbamoyl 1 1.248 550.9 I-49#—CH₂—S(═O)₂—CH₂—* [(4S)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.266 623.6yl]carbamoyl I-50 #—CH₂—S(═O)₂—CH₂—* thietan-3-ylcarbamoyl 1 1.322 582.5I-51 #—CH₂—S—CH₂—* (1,1-dioxothietan-3-yl)carbamoyl 1 1.380 580.8 I-52#—CH₂—S—CH₂—* pyrimidin-2-ylmethylcarbamoyl 1 1.333 571.0 I-53#—CH₂—S(═O)₂—CH₂—* (1,1-dioxothietan-3-yl)carbamoyl 1 1.332 564.6 I-54#—CH₂—S(═O)₂—CH₂—* [(4R)-2-ethyl-3-oxo-isoxazolidin-4- 1 1.249 624.0yl]carbamoyl I-58 #—CH₂—CH₂—CH₂—O—* (butanoylamino)methyl 1 1.344519.1^(a) ^(a1)H-NMR of I-58 (400 MHz, CDCl₃): δ = 1.15 (m, 3H),1.94-2.08 (m, 2H), 2.22 (m, 2H), 3.01 (m, 2H), 3.73 (d, 1H), 4.09 (d,1H), 4.18-4.29 (m, 2H), 4.40 (d, 2H), 5.97 (m, 1H), 6.85 (d, 1H), 7.17(d, 1H), 7.58 (m, 2H). #attachment point in position of R^(g1)*attachment point in position of R^(g2)

TABLE C.2 compounds of formula I-A with R^(2a) = R^(2c) = Cl, R^(2b) = Ht_(R) m/z No. R^(g1) R^(g2) A method [min] [M + H]⁺ I-56 #—O—CH₂—O—*pyrimidin-2-ylmethylcarbamoyl 1 1.272 539.0 I-57 #—CH₂—CH₂—CH₂—O—*pyrimidin-2-ylmethylcarbamoyl 1 1.377 552.4

II. Evaluation of Pesticidal Activity

The activity of the compounds of formula I of the present invention canbe demonstrated and evaluated by the following biological test.

B.1 Diamond Back Moth (Plutella xylostella)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol).The test solution wasprepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treatedleaves were placed in petri dishes lined with moist filter paper andinoculated with ten 3^(rd) instar larvae. Mortality was recorded 72hours after treatment. Feeding damages were also recorded using a scaleof 0-100%.

In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9,I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21,I-22, I-23, I-24, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36,I-37, I-38, I-39, I-41, I-42, I-44, I-46, I-47, I-48, I-51, I-52, I-56,I-57 at 300 ppm showed at least 75% mortality in comparison withuntreated controls.

B.2 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) throughsystemic means the test unit consisted of 96-well-microtiter platescontaining liquid artificial diet under an artificial membrane.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds werepipetted into the aphid diet, using a custom built pipetter, at tworeplications.

After application, 5-8 adult aphids were placed on the artificialmembrane inside the microtiter plate wells. The aphids were then allowedto suck on the treated aphid diet and incubated at about 23±1° C. andabout 50±5% relative humidity for 3 days. Aphid mortality and fecunditywas then visually assessed.

In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9,I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21,I-22, I-23, I-24, I-26, I-28, I-30, I-31, I-32, I-33, I-34, I-37, I-41,I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, I-50, I-54, I-56, I-57at 2500 ppm showed at least 75% mortality in comparison with untreatedcontrols.

B.3 Vetch Aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consisted of 24-well-microtiter platescontaining broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the leaf disks at 2.5 μl, using a custom built microatomizer, at two replications.

After application, the leaf disks were air-dried and 5-8 adult aphidsplaced on the leaf disks inside the microtiter plate wells. The aphidswere then allowed to suck on the treated leaf disks and incubated atabout 23±10C and about 50±5% relative humidity for 5 days. Aphidmortality and fecundity was then visually assessed.

In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9,I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21,I-22, I-23, I-24, I-28, I-30, I-31, I-32, I-33, I-34, I-37, I-41, I-43,I-46, I-47, I-48, I-50, I-54 at 2500 ppm showed at least 75% mortalityin comparison with untreated controls.

B.4 Tobacco Budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consisted of 96-well-microtiter plates containing an insect dietand 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 10 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 28±10C andabout 80±5% relative humidity for 5 days. Egg and larval mortality wasthen visually assessed.

In this test, compounds I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9,I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21,I-22, I-23, I-24, I-26, I-28, I-30, I-31, I-32, I-33, I-34, I-37, I-40,I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, I-50, I-54, I-56,I-57 at 2500 ppm showed at least 75% mortality in comparison withuntreated controls.

B.5 Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unitconsisted of 96-well-microtiter plates containing an insect diet and5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 5 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 25±1° C.and about 75±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11,I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23,I-24, I-26, I-27, I-28, I-30, I-31, I-32, I-33, I-34, I-37, I-40, I-41,I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, I-50, I-54, I-56, I-57at 2500 ppm showed at least 75% mortality in comparison with untreatedcontrols.

B.6 Mediterranean Fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata)the test unit consisted of microtiter plates containing an insect dietand 50-80 C. capitata eggs. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the insect dietat 5 μl, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80+5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11,I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23,I-24, I-28, I-30, I-31, I-32, I-33, I-34, I-37, I-40, I-41, I-42, I-43,I-44, I-45, I-46, I-47, I-48, I-49, I-50, I-54 at 2500 ppm showed atleast 75% mortality in comparison with untreated controls.

B.7 Orchid Thrips (Dichromothrips Corbetti) Dichromothripscorbettiadults used for bioassay were obtained from a colony maintainedcontinuously under laboratory conditions. For testing purposes, the testcompound is diluted in a 1:1 mixture of acetone:water (vol:vol), plusKinetic HV at a rate of 0.01% v/v.

Thrips potency of each compound was evaluated by using afloral-immersion technique. All petals of individual, intact orchidflowers were dipped into treatment solution and allowed to dry in Petridishes. Treated petals were placed into individual re-sealable plasticalong with about 20 adult thrips. All test arenas were held undercontinuous light and a temperature of about 28° C. for duration of theassay. After 3 days, the numbers of live thrips were counted on eachpetal. The percent mortality was recorded 72 hours after treatment.

In this test, I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11,I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23,I-24, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-37, I-38,I-39, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, I-50,I-51, I-52, I-53, I-54, I-56, I-57 at 300 ppm showed at least 75%mortality in comparison with untreated controls.

B.8 Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. Theactive compounds were formulated in 1:1 acetone:water (vol:vol), and0.01% vol/vol surfactant (Kinetic HV) was added. Potted rice seedlingswere sprayed with 5-6 ml test solution, air dried, covered with Mylarcages cages and inoculated with 10 adults. Treated rice plants were keptat about 28-29° C. and relative humidity of about 50-60%. Percentmortality was recorded after 72 hours.

In this test, I-1, I-2, I-4, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-14,I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23, I-24, I-28, I-30,I-31, I-33, I-34, I-36, I-37, I-38, I-39, I-52 at 300 ppm showed atleast 75% mortality in comparison with untreated controls.

B.9 Red Spider Mite (Tetranychus kanzawai)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Add surfactant(Kinetic HV) was added at a rate of 0.01% (vol/vol).The test solutionwas prepared at the day of use.

Potted cowpea beans of 4-5 days of age were cleaned with tap water andsprayed with 1-2 ml of the test solution using air driven hand atomizer.The treated plants were allowed to air dry and afterwards inoculatedwith 30 or more mites by clipping a cassava leaf section from rearingpopulation. Treated plants were placed inside a holding room at about25-27° C. and about 50-60% relative humidity. Percent mortality wasassessed 72 hours after treatment.

In this test, I-7, I-9, I-11, I-14, I-15, I-16, I-17, I-18, I-19, I-20,I-21, I-22, I-23, I-28, I-29, I-34, I-54 at 300 ppm showed at least 75%mortality in comparison with untreated controls.

B.10 Southern Armyworm (Spodoptera eridania)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Lima bean plants (variety Sieva) were grown 2 plants to a pot andselected for treatment at the 1^(st) true leaf stage. Test solutionswere sprayed onto the foliage by an automated electrostatic plantsprayer equipped with an atomizing spray nozzle. The plants were driedin the sprayer fume hood and then removed from the sprayer. Each pot wasplaced into perforated plastic bags with a zip closure. About 10 to 11armyworm larvae were placed into the bag and the bags zipped closed.Test plants were maintained in a growth room at about 250C and about20-40% relative humidity for 4 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the bags. Mortality and reduced feeding were assessed 4 daysafter treatment, compared to untreated control plants.

In this test, I-6, I-7, I-9, I-10, I-11, I-15, I-17, I-18, I-20, I-21,I-33, I-34, I-37, I-38, I-39, I-42, I-43, I-47, I-48 at 10 ppm showed atleast 75% mortality in comparison with untreated controls.

B.11 Green Soldier Stink Bug (Nezara viridula)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol).The test solution wasprepared at the day of use.

Soybean pods were placed in glass Petri dishes lined with moist filterpaper and inoculated with ten late 3rd instar N. viridula. Using a handatomizer, approximately 2 ml solution is sprayed into each Petri dish.Assay arenas were kept at about 25° C. Percent mortality was recordedafter 5 days.

In this test, I-1, I-2, I-3, I-4, I-6, I-7, I-8, I-9, I-10, I-11, I-13,I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23, I-28, I-29,I-33, I-34 at 300 ppm showed at least 75% mortality in comparison withuntreated controls.

B.12 Neotropical Brown Stink Bug (Euschistus heros)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol).The test solution wasprepared at the day of use.

Soybean pods were placed in microwavable plastic cups and inoculatedwith ten adult stage E. heros. Using a hand atomizer, approximately 1 mlsolution is sprayed into each cup, insects and food present. A watersource was provided (cotton wick with water). Each treatment wasreplicated 2-fold. Assay arenas were kept at about 25° C. Percentmortality was recorded after 5 days.

In this test, I-1, I-2, I-6, I-7, I-9, I-10, I-11, I-15, I-17, I-18,I-20, I-23 at 100 ppm showed at least 75% mortality in comparison withuntreated controls.

B.13 Brown Marmorated Stink Bug (Halyomorpha halys)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol).The test solution wasprepared at the day of use.

Row peanuts and soybean seeds were placed into microwavable plastic cupsand inoculated with five adult stage H. halys. Using a hand atomizer,approximately 1 ml solution is sprayed into each cup, insects and foodpresent. A water source was provided (cotton wick with water). Eachtreatment is replicated 4-fold. Assay arenas are kept at about 25° C.Percent mortality was recorded after 5 days.

In this test 1-6, I-7, I-8, I-9, I-15, I-17, I-18, I-20, I-21, I-34,I-37 at 100 ppm showed at least 75% mortality in comparison withuntreated controls.

We claim:
 1. A compound of formula (Ia.21)

wherein R^(2a), R^(2b) and R^(2c), independently of each other, areselected from the group consisting of hydrogen, halogen,C₁-C₂-haloalkoxy, and C₁-C₂-haloalkyl; and R⁶² is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsubstituted by one or two radicals R⁸², C₁-C₆-haloalkyl which carriesone radical R⁸², C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which carries a CNsubstituent, C₃-C₆-halocycloalkyl, —N(R^(102a))R^(102b),—C(═O)N(R^(112a))R^(112b), —CH═NOR⁹², phenyl, phenyl which issubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a heterocyclicring selected from the group consisting of rings of formulae E-1 toE-63:

wherein rings E-1 to E-63 the zigzag line denotes the attachment pointto the remainder of the molecule; k is 0, 1, 2 or 3; n is 0, 1 or 2; andR¹⁶ is as defined below; each R⁸² is independently selected from thegroup consisting of OH, CN, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl whichcarries a CN or C₁-haloalkyl substituent, C₃-C₆-halocycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102c))R^(102d), phenyl, phenylsubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclicring selected from the group consisting of rings E-1 to E-63 as definedabove; R⁹² is selected from the group consisting of hydrogen,C₁-C₆-alkyl, and C₁-C₆-haloalkyl; R^(102a), R^(102c) and R^(112a),independently of each other, are selected from the group consisting ofhydrogen and C₁-C₆-alkyl; R^(102b) is selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, CH₂—CN, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkylmethyl, C₃-C₆-halocycloalkylmethyl, phenyl, phenylsubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶; and a heterocyclicring selected from the group consisting of rings of formulae E-1 to E-42as defined above; R^(102d) and R^(112b), independently of each other,are selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which carries a CNsubstituent, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl andC₃-C₆-halocycloalkylmethyl; each R¹⁶ is independently selected from thegroup consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-halocycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶present on the same carbon atom of a saturated ring may form together ═Oor ═S; or two R¹⁶ present on the same S or SO ring member of aheterocyclic ring may together form a group ═N(C₁-C₆-alkyl),═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂; or anN-oxide, stereoisomer, or an agriculturally or veterinarily acceptablesalt thereof.
 2. The compound as claimed in claim 1, wherein R^(2a),R^(2b) and R^(2c), independently of each other, are selected from thegroup consisting of hydrogen, halogen, OCF₃ and CF₃.
 3. The compound asclaimed in claim 2, wherein R^(2a), R^(2b) and R^(2c), independently ofeach other, are selected from the group consisting of hydrogen andhalogen.
 4. The compound as claimed in claim 3, wherein R^(2a), R^(2b)and R^(2c), independently of each other, are selected from the groupconsisting of hydrogen, F and Cl.
 5. The compound as claimed in claim 4,wherein R^(2a) is Cl, R^(2b) is H and R^(2c) is Cl; or R^(2a) is Cl,R^(2b) is F and R^(2c) is H; or R^(2a) is Cl, R^(2b) is F and R^(2c) isCl.
 6. The compound as claimed in claim 1, wherein R⁶² is selected fromthe group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkyl substituted by one or two radicals R⁸², C₁-C₆-haloalkylwhich carries one radical R⁸², C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl whichcarries a CN substituent, and C₃-C₆-halocycloalkyl.
 7. The compound asclaimed in claim 6, wherein R⁶² is selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkyl substituted by oneradical R⁸², C₃-C₆-cycloalkyl, and C₃-C₆-cycloalkyl which carries a CNsubstituent.
 8. The compound as claimed in claim 1, wherein R⁸² isselected from the group consisting of C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl andC₁-C₆-haloalkylsulfonyl.
 9. The compound as claimed in claim 7, whereinR⁶² is selected from the group consisting of methyl, ethyl, n-propyl,cyclopropyl, —CH₂CF₃, —CH₂SCH₃, —CH₂SCH₂CH₃, —CH₂S(O)CH₃,—CH₂S(O)CH₂CH₃, —CH₂S(O)₂CH₃, —CH₂S(O)₂CH₂CH₃, —CH₂OCH₃, and—CH₂CH₂OCH₃.
 10. The compound as claimed in claim 1, wherein R^(2a) isCl, R^(2b) is H and R^(2c) is Cl; and R⁶² is selected from the groupconsisting of methyl, ethyl, n-propyl, cyclopropyl, —CH₂CF₃, —CH₂SCH₃,—CH₂SCH₂CH₃, —CH₂S(O)CH₃, —CH₂S(O)CH₂CH₃, —CH₂S(O)₂CH₃, —CH₂S(O)₂CH₂CH₃,—CH₂OCH₃, and —CH₂CH₂OCH₃; or R^(2a) is Cl, R^(2b) is F and R^(2c) is H;and R⁶² is selected from the group consisting of methyl, ethyl,n-propyl, cyclopropyl, —CH₂CF₃, —CH₂SCH₃, —CH₂SCH₂CH₃, —CH₂S(O)CH₃,—CH₂S(O)CH₂CH₃, —CH₂S(O)₂CH₃, —CH₂S(O)₂CH₂CH₃, —CH₂OCH₃, and—CH₂CH₂OCH₃; or R^(2a) is Cl, R^(2b) is F and R^(2c) is Cl; and R⁶² isselected from the group consisting of methyl, ethyl, n-propyl,cyclopropyl, —CH₂CF₃, —CH₂SCH₃, —CH₂SCH₂CH₃, —CH₂S(O)CH₃,—CH₂S(O)CH₂CH₃, —CH₂S(O)₂CH₃, —CH₂S(O)₂CH₂CH₃, —CH₂OCH₃, and—CH₂CH₂OCH₃.
 11. The compound as claimed in claim 1, wherein R^(2a) isCl, R^(2b) is F and R^(2c) is Cl; and R⁶² is —CH₂CH₂CH₃; or R^(2a) isCl, R^(2b) is F and R^(2c) is Cl; and R⁶² is —CH₂CH₃; or R^(2a) is Cl,R^(2b) is F and R^(2c) is Cl; and R⁶² is —CH₃; or R^(2a) is Cl, R^(2b)is F and R^(2c) is Cl; and R⁶² is —CH₂S(O)₂CH₂CH₃; or R^(2a) is Cl,R^(2b) is F and R^(2c) is Cl; and R⁶² is —CH₂S(O)₂CH₃; or R^(2a) is Cl,R^(2b) is F and R^(2c) is Cl; and R⁶² is cyclopropyl.
 12. The compoundas claimed in claim 1, wherein R^(2a) is C₁, R^(2b) is H and R^(2c) isCl; and R⁶² is —CH₂CH₂CH₃; or R^(2a) is Cl, R^(2b) is H and R^(2c) isCl; and R⁶² is —CH₂CH₃; or R^(2a) is C₁, R^(2b) is H and R^(2c) is Cl;and R⁶² is —CH₃; or R^(2a) is Cl, R^(2b) is H and R^(2c) is Cl; and R⁶²is —CH₂S(O)₂CH₂CH₃; or R^(2a) is Cl, R^(2b) is H and R^(2c) is Cl; andR⁶² is —CH₂S(O)₂CH₃; or R^(2a) is Cl, R^(2b) is H and R^(2c) is Cl; andR⁶² is cyclopropyl.
 13. An agricultural or veterinary compositioncomprising at least one compound of the formula Ia.21 as defined inclaim 1, a stereoisomer thereof and/or at least one agriculturally orveterinarily acceptable salt thereof, and at least one inert liquidand/or solid agriculturally or veterinarily acceptable carrier.
 14. Theagricultural composition according to claim 13, further a surfactant.15. The agricultural or veterinary composition according to claim 13,comprising additionally a further active ingredient.
 16. A method forcontrolling invertebrate pests, which method comprises treating thepests, their food supply, their habitat or their breeding ground or acultivated plant, plant propagation materials (such as seed), soil,area, material or environment in which the pests are growing or maygrow, or the materials, cultivated plants, plant propagation materials,soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula Ia.21 as defined in claim 1, a stereoisomer thereof and/or atleast one agriculturally acceptable salt thereof.
 17. A method forprotecting plant propagation material and/or the plants which growtherefrom from attack or infestation by invertebrate pests, which methodcomprises treating the plant propagation material with a pesticidallyeffective amount of at least one compound of the formula Ia.21 asdefined in claim 1, a stereoisomer thereof and/or at least oneagriculturally acceptable salt thereof.
 18. A method for treating orprotecting an animal from infestation or infection by invertebratepests, which method comprises bringing the animal in contact with apesticidally effective amount of a compound of the formula Ia.21 asdefined in claim 1, a stereoisomer thereof and/or at least oneveterinarily acceptable salt thereof.
 19. A seed treated with at leastone compound of the formula Ia.21 as defined in claim 1, a stereoisomerthereof and/or at least one agriculturally acceptable salt thereof, inan amount of from 0.01 g to 10 kg per 100 kg of seed.